HRP980056A2 - Efficient synthesis of a 1,4-dihidro-2h-3,1-benzoxazin-2-one - Google Patents

Efficient synthesis of a 1,4-dihidro-2h-3,1-benzoxazin-2-one

Info

Publication number: HRP980056A2
Authority: HR; Croatia
Prior art keywords: benzoxazin; dihydro; preparation; alkyl; chloroformate
Prior art date: 1997-02-12

Application number

HR9706082.6A

Other languages

English (en)

Croatian (hr)

Inventor

Edward J J Grabowski

Original Assignee

Edward J.J: Grabowski

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1997-02-12

Filing date

1998-02-04

Publication date

1998-12-31

1997-03-24 Priority claimed from GBGB9706082.6A external-priority patent/GB9706082D0/en

1998-02-04 Application filed by Edward J.J: Grabowski filed Critical Edward J.J: Grabowski

1998-12-31 Publication of HRP980056A2 publication Critical patent/HRP980056A2/hr

Links

230000015572 biosynthetic process Effects 0.000 title claims description 15
238000003786 synthesis reaction Methods 0.000 title description 4
SYZIUAAQNFJPJY-UHFFFAOYSA-N 1,4-dihydro-3,1-benzoxazin-2-one Chemical compound C1=CC=C2COC(=O)NC2=C1 SYZIUAAQNFJPJY-UHFFFAOYSA-N 0.000 claims description 75
238000000034 method Methods 0.000 claims description 67
238000002360 preparation method Methods 0.000 claims description 63
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 42
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 42
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 34
239000002904 solvent Substances 0.000 claims description 32
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 31
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 31
-1 aryl chloroformate Chemical compound 0.000 claims description 31
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 30
239000007787 solid Substances 0.000 claims description 29
239000000203 mixture Substances 0.000 claims description 28
239000003960 organic solvent Substances 0.000 claims description 28
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 27
KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 27
238000006243 chemical reaction Methods 0.000 claims description 24
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 23
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 22
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 21
239000012071 phase Substances 0.000 claims description 21
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 20
235000015497 potassium bicarbonate Nutrition 0.000 claims description 20
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 claims description 20
239000011736 potassium bicarbonate Substances 0.000 claims description 19
229910000028 potassium bicarbonate Inorganic materials 0.000 claims description 19
239000011541 reaction mixture Substances 0.000 claims description 18
235000015320 potassium carbonate Nutrition 0.000 claims description 16
229910000027 potassium carbonate Inorganic materials 0.000 claims description 16
235000011118 potassium hydroxide Nutrition 0.000 claims description 16
125000003118 aryl group Chemical group 0.000 claims description 15
238000003756 stirring Methods 0.000 claims description 15
125000001475 halogen functional group Chemical group 0.000 claims description 14
125000001424 substituent group Chemical group 0.000 claims description 14
238000002425 crystallisation Methods 0.000 claims description 13
230000008025 crystallization Effects 0.000 claims description 13
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 12
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 claims description 12
FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 claims description 12
235000017557 sodium bicarbonate Nutrition 0.000 claims description 12
239000012074 organic phase Substances 0.000 claims description 11
238000007363 ring formation reaction Methods 0.000 claims description 11
229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 11
235000011121 sodium hydroxide Nutrition 0.000 claims description 11
NXLNNXIXOYSCMB-UHFFFAOYSA-N (4-nitrophenyl) carbonochloridate Chemical compound [O-][N+](=O)C1=CC=C(OC(Cl)=O)C=C1 NXLNNXIXOYSCMB-UHFFFAOYSA-N 0.000 claims description 10
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical group CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 10
230000029142 excretion Effects 0.000 claims description 10
238000010791 quenching Methods 0.000 claims description 10
235000017550 sodium carbonate Nutrition 0.000 claims description 10
229910000029 sodium carbonate Inorganic materials 0.000 claims description 10
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 10
150000001414 amino alcohols Chemical class 0.000 claims description 9
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
230000000171 quenching effect Effects 0.000 claims description 9
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 8
239000012298 atmosphere Substances 0.000 claims description 8
239000012455 biphasic mixture Substances 0.000 claims description 8
ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 claims description 8
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 7
125000000217 alkyl group Chemical group 0.000 claims description 7
239000012296 anti-solvent Substances 0.000 claims description 6
KWHDXJHBFYQOTK-UHFFFAOYSA-N heptane;toluene Chemical compound CCCCCCC.CC1=CC=CC=C1 KWHDXJHBFYQOTK-UHFFFAOYSA-N 0.000 claims description 6
229910052808 lithium carbonate Inorganic materials 0.000 claims description 6
XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 claims description 6
229910000032 lithium hydrogen carbonate Inorganic materials 0.000 claims description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 5
125000001624 naphthyl group Chemical group 0.000 claims description 5
125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 4
239000002253 acid Substances 0.000 claims description 4
AHWALFGBDFAJAI-UHFFFAOYSA-N phenyl carbonochloridate Chemical compound ClC(=O)OC1=CC=CC=C1 AHWALFGBDFAJAI-UHFFFAOYSA-N 0.000 claims description 4
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 3
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 claims description 3
YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical compound [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 claims description 3
LZWQNOHZMQIFBX-UHFFFAOYSA-N lithium;2-methylpropan-2-olate Chemical compound [Li+].CC(C)(C)[O-] LZWQNOHZMQIFBX-UHFFFAOYSA-N 0.000 claims description 3
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 2
XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical group COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 claims description 2
229910017604 nitric acid Inorganic materials 0.000 claims description 2
239000012299 nitrogen atmosphere Substances 0.000 claims description 2
IUBQJLUDMLPAGT-UHFFFAOYSA-N potassium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([K])[Si](C)(C)C IUBQJLUDMLPAGT-UHFFFAOYSA-N 0.000 claims description 2
WRIKHQLVHPKCJU-UHFFFAOYSA-N sodium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([Na])[Si](C)(C)C WRIKHQLVHPKCJU-UHFFFAOYSA-N 0.000 claims description 2
235000011149 sulphuric acid Nutrition 0.000 claims description 2
OBUNLFQVPAABFB-UHFFFAOYSA-N ethoxyethane;heptane Chemical compound CCOCC.CCCCCCC OBUNLFQVPAABFB-UHFFFAOYSA-N 0.000 claims 1
238000000926 separation method Methods 0.000 claims 1
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 22
239000000243 solution Substances 0.000 description 19
239000002002 slurry Substances 0.000 description 18
239000010410 layer Substances 0.000 description 15
239000000725 suspension Substances 0.000 description 14
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
229910052757 nitrogen Inorganic materials 0.000 description 11
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
XPOQHMRABVBWPR-ZDUSSCGKSA-N efavirenz Chemical compound C([C@]1(C2=CC(Cl)=CC=C2NC(=O)O1)C(F)(F)F)#CC1CC1 XPOQHMRABVBWPR-ZDUSSCGKSA-N 0.000 description 10
238000004128 high performance liquid chromatography Methods 0.000 description 10
GTCAXTIRRLKXRU-UHFFFAOYSA-N methyl carbamate Chemical compound COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 description 10
239000012267 brine Substances 0.000 description 7
239000000047 product Substances 0.000 description 7
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 7
JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 6
239000012044 organic layer Substances 0.000 description 6
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 5
229910052943 magnesium sulfate Inorganic materials 0.000 description 5
235000019341 magnesium sulphate Nutrition 0.000 description 5
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
229910000041 hydrogen chloride Inorganic materials 0.000 description 4
239000012452 mother liquor Substances 0.000 description 4
239000007858 starting material Substances 0.000 description 4
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 3
150000001875 compounds Chemical class 0.000 description 3
238000001816 cooling Methods 0.000 description 3
239000013078 crystal Substances 0.000 description 3
IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
239000000126 substance Substances 0.000 description 3
238000005160 1H NMR spectroscopy Methods 0.000 description 2
IQUPABOKLQSFBK-UHFFFAOYSA-N 2-nitrophenol Chemical compound OC1=CC=CC=C1[N+]([O-])=O IQUPABOKLQSFBK-UHFFFAOYSA-N 0.000 description 2
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 2
238000001914 filtration Methods 0.000 description 2
YEMWINDXAKRPBK-UHFFFAOYSA-N heptane;2-methoxy-2-methylpropane Chemical compound COC(C)(C)C.CCCCCCC YEMWINDXAKRPBK-UHFFFAOYSA-N 0.000 description 2
239000012535 impurity Substances 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
238000002156 mixing Methods 0.000 description 2
OKXGHXHZNCJMSV-UHFFFAOYSA-N nitro phenyl carbonate Chemical compound [O-][N+](=O)OC(=O)OC1=CC=CC=C1 OKXGHXHZNCJMSV-UHFFFAOYSA-N 0.000 description 2
238000010915 one-step procedure Methods 0.000 description 2
239000003419 rna directed dna polymerase inhibitor Substances 0.000 description 2
239000011734 sodium Substances 0.000 description 2
239000006228 supernatant Substances 0.000 description 2
FRQWVAWXEBTURS-UHFFFAOYSA-N (2-nitrophenyl) carbamate Chemical compound NC(=O)OC1=CC=CC=C1[N+]([O-])=O FRQWVAWXEBTURS-UHFFFAOYSA-N 0.000 description 1
FHLXUWOHGKLDNF-UHFFFAOYSA-N (2-nitrophenyl) carbonochloridate Chemical compound [O-][N+](=O)C1=CC=CC=C1OC(Cl)=O FHLXUWOHGKLDNF-UHFFFAOYSA-N 0.000 description 1
HQQTZCPKNZVLFF-UHFFFAOYSA-N 4h-1,2-benzoxazin-3-one Chemical compound C1=CC=C2ONC(=O)CC2=C1 HQQTZCPKNZVLFF-UHFFFAOYSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
YZDAFWLIMRVDNP-UHFFFAOYSA-N acetonitrile;n,n-dimethylacetamide Chemical compound CC#N.CN(C)C(C)=O YZDAFWLIMRVDNP-UHFFFAOYSA-N 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
229910052786 argon Inorganic materials 0.000 description 1
238000011914 asymmetric synthesis Methods 0.000 description 1
239000000872 buffer Substances 0.000 description 1
239000007853 buffer solution Substances 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
150000004657 carbamic acid derivatives Chemical class 0.000 description 1
150000001721 carbon Chemical group 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
VWWMOACCGFHMEV-UHFFFAOYSA-N dicarbide(2-) Chemical compound [C-]#[C-] VWWMOACCGFHMEV-UHFFFAOYSA-N 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
MJDDHOXHJDDWBP-UHFFFAOYSA-N ethynylcyclopropane Chemical compound [C-]#CC1CC1 MJDDHOXHJDDWBP-UHFFFAOYSA-N 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000007789 gas Substances 0.000 description 1
125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
VBZWSGALLODQNC-UHFFFAOYSA-N hexafluoroacetone Chemical compound FC(F)(F)C(=O)C(F)(F)F VBZWSGALLODQNC-UHFFFAOYSA-N 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
239000012456 homogeneous solution Substances 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
239000003999 initiator Substances 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
231100000614 poison Toxicity 0.000 description 1
230000007096 poisonous effect Effects 0.000 description 1
235000011181 potassium carbonates Nutrition 0.000 description 1
OZYMELGGTSHIOM-UHFFFAOYSA-N potassium sodium bis(trimethylsilyl)azanide Chemical compound C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[K+].C[Si]([N-][Si](C)(C)C)(C)C OZYMELGGTSHIOM-UHFFFAOYSA-N 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000006798 ring closing metathesis reaction Methods 0.000 description 1
238000005070 sampling Methods 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
235000011182 sodium carbonates Nutrition 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/04—1,3-Oxazines; Hydrogenated 1,3-oxazines
- C07D265/12—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems
- C07D265/14—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D265/18—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring with hetero atoms directly attached in position 2
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/26—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic ring
- C07C271/28—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic ring to a carbon atom of a non-condensed six-membered aromatic ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/02—Systems containing only non-condensed rings with a three-membered ring

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

HR9706082.6A 1997-02-12 1998-02-04 Efficient synthesis of a 1,4-dihidro-2h-3,1-benzoxazin-2-one HRP980056A2 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US3705997P	1997-02-12	1997-02-12
GBGB9706082.6A GB9706082D0 (en)	1997-03-24	1997-03-24	Efficient synthesis of A 1,4-dihydro-2H-3,1-benzoxazin-2-one

Publications (1)

Publication Number	Publication Date
HRP980056A2 true HRP980056A2 (en)	1998-12-31

Family

ID=26311250

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
HR9706082.6A HRP980056A2 (en)	1997-02-12	1998-02-04	Efficient synthesis of a 1,4-dihidro-2h-3,1-benzoxazin-2-one

Country Status (13)

Country	Link
EP (1)	EP0968197B1 (de)
CN (1)	CN1073992C (de)
AR (1)	AR011128A1 (de)
AT (1)	ATE294165T1 (de)
AU (1)	AU6152598A (de)
BR (1)	BR9807213A (de)
DE (1)	DE69829956T2 (de)
EA (1)	EA001784B1 (de)
ES (1)	ES2239798T3 (de)
HR (1)	HRP980056A2 (de)
SK (1)	SK108999A3 (de)
TW (1)	TW480253B (de)
WO (1)	WO1998034928A1 (de)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6015926A (en) *	1997-05-16	2000-01-18	Merck & Co., Inc.	Efficient enantioselective addition reaction using an organozinc reagent
PE20060587A1 (es) *	2004-09-02	2006-07-09	Bristol Myers Squibb Co	Sintesis de (s)-6-cloro-4-ciclopropiletinil-4-trifluorometil-1,4-dihidro-2h-3,1-benzoxazin-2-ona

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5633405A (en) *	1995-05-25	1997-05-27	Merck & Co., Inc.	Asymmetric synthesis of (-)-6-chloro-4-cyclopropyl-ethynyl-4-trifluoromethyl-1,4-dihydro-2H-3,1-benzoxanzin-2-one

1998
- 1998-02-04 TW TW087101435A patent/TW480253B/zh not_active IP Right Cessation
- 1998-02-04 HR HR9706082.6A patent/HRP980056A2/hr not_active Application Discontinuation
- 1998-02-09 WO PCT/US1998/002495 patent/WO1998034928A1/en not_active Ceased
- 1998-02-09 EA EA199900736A patent/EA001784B1/ru not_active IP Right Cessation
- 1998-02-09 ES ES98906255T patent/ES2239798T3/es not_active Expired - Lifetime
- 1998-02-09 DE DE69829956T patent/DE69829956T2/de not_active Expired - Lifetime
- 1998-02-09 SK SK1089-99A patent/SK108999A3/sk unknown
- 1998-02-09 AT AT98906255T patent/ATE294165T1/de not_active IP Right Cessation
- 1998-02-09 AU AU61525/98A patent/AU6152598A/en not_active Abandoned
- 1998-02-09 CN CN98802445A patent/CN1073992C/zh not_active Expired - Fee Related
- 1998-02-09 EP EP98906255A patent/EP0968197B1/de not_active Expired - Lifetime
- 1998-02-09 BR BR9807213-7A patent/BR9807213A/pt not_active IP Right Cessation
- 1998-02-10 AR ARP980100589A patent/AR011128A1/es not_active Application Discontinuation

Also Published As

Publication number	Publication date
EA199900736A1 (ru)	2000-02-28
EP0968197B1 (de)	2005-04-27
ATE294165T1 (de)	2005-05-15
AU6152598A (en)	1998-08-26
TW480253B (en)	2002-03-21
SK108999A3 (en)	2000-05-16
ES2239798T3 (es)	2005-10-01
DE69829956T2 (de)	2006-03-02
WO1998034928A1 (en)	1998-08-13
AR011128A1 (es)	2000-08-02
DE69829956D1 (de)	2005-06-02
CN1246852A (zh)	2000-03-08
CN1073992C (zh)	2001-10-31
BR9807213A (pt)	2000-05-23
EA001784B1 (ru)	2001-08-27
EP0968197A1 (de)	2000-01-05

Legal Events

Date	Code	Title
1998-12-31	A1OB	Publication of a patent application
1999-06-11	AIPI	Request for the grant of a patent on the basis of a substantive examination of a patent application
2006-04-06	ODBC	Application rejected

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