IL88064A - Large scale synthesis of twelve member diazamonocyclic compounds and some such novel compounds - Google Patents

Large scale synthesis of twelve member diazamonocyclic compounds and some such novel compounds

Info

Publication number: IL88064A
Authority: IL; Israel
Prior art keywords: solvent; compound; formula; compounds; benzene
Prior art date: 1987-12-14

Application number

IL8806488A

Other languages

English (en)

Other versions

IL88064A0 (en

Original Assignee

Technicon Instr

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.)

1987-12-14

Filing date

1988-10-17

Publication date

1994-02-27

1988-10-17 Application filed by Technicon Instr filed Critical Technicon Instr

1989-06-30 Publication of IL88064A0 publication Critical patent/IL88064A0/xx

1994-02-27 Publication of IL88064A publication Critical patent/IL88064A/en

Links

150000001875 compounds Chemical class 0.000 title claims description 32
238000003786 synthesis reaction Methods 0.000 title description 17
230000015572 biosynthetic process Effects 0.000 title description 16
UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 47
239000002904 solvent Substances 0.000 claims description 25
238000000034 method Methods 0.000 claims description 24
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 18
230000008569 process Effects 0.000 claims description 17
125000000217 alkyl group Chemical group 0.000 claims description 15
238000006243 chemical reaction Methods 0.000 claims description 15
125000003118 aryl group Chemical group 0.000 claims description 13
125000001118 alkylidene group Chemical group 0.000 claims description 12
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 11
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 10
239000001257 hydrogen Substances 0.000 claims description 8
229910052739 hydrogen Inorganic materials 0.000 claims description 8
125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 claims description 5
238000004519 manufacturing process Methods 0.000 claims description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 4
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 3
-1 e.g. Substances 0.000 description 11
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
125000003342 alkenyl group Chemical group 0.000 description 7
239000007795 chemical reaction product Substances 0.000 description 7
238000010790 dilution Methods 0.000 description 7
239000012895 dilution Substances 0.000 description 7
239000000376 reactant Substances 0.000 description 7
239000000243 solution Substances 0.000 description 7
GXVUZYLYWKWJIM-UHFFFAOYSA-N 2-(2-aminoethoxy)ethanamine Chemical compound NCCOCCN GXVUZYLYWKWJIM-UHFFFAOYSA-N 0.000 description 6
239000000758 substrate Substances 0.000 description 6
150000002431 hydrogen Chemical class 0.000 description 5
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
239000000706 filtrate Substances 0.000 description 4
239000000203 mixture Substances 0.000 description 4
PWJHXHMUGFXPSN-UHFFFAOYSA-N 1,7-dioxa-4,10-diazacyclododecane Chemical compound C1COCCNCCOCCN1 PWJHXHMUGFXPSN-UHFFFAOYSA-N 0.000 description 3
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 3
239000012346 acetyl chloride Substances 0.000 description 3
125000004432 carbon atom Chemical group C* 0.000 description 3
239000003153 chemical reaction reagent Substances 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
239000000047 product Substances 0.000 description 3
239000007787 solid Substances 0.000 description 3
238000005406 washing Methods 0.000 description 3
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
QEVGZEDELICMKH-UHFFFAOYSA-N Diglycolic acid Chemical compound OC(=O)COCC(O)=O QEVGZEDELICMKH-UHFFFAOYSA-N 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
239000002739 cryptand Substances 0.000 description 2
125000004122 cyclic group Chemical group 0.000 description 2
238000003113 dilution method Methods 0.000 description 2
125000006575 electron-withdrawing group Chemical group 0.000 description 2
239000000543 intermediate Substances 0.000 description 2
239000012280 lithium aluminium hydride Substances 0.000 description 2
150000002678 macrocyclic compounds Chemical class 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
238000003756 stirring Methods 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
NLMDJJTUQPXZFG-UHFFFAOYSA-N 1,4,10,13-tetraoxa-7,16-diazacyclooctadecane Chemical compound C1COCCOCCNCCOCCOCCN1 NLMDJJTUQPXZFG-UHFFFAOYSA-N 0.000 description 1
125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
RMSGQZDGSZOJMU-UHFFFAOYSA-N 1-butyl-2-phenylbenzene Chemical group CCCCC1=CC=CC=C1C1=CC=CC=C1 RMSGQZDGSZOJMU-UHFFFAOYSA-N 0.000 description 1
125000006017 1-propenyl group Chemical group 0.000 description 1
JONTXEXBTWSUKE-UHFFFAOYSA-N 2-(2-aminoethylsulfanyl)ethanamine Chemical compound NCCSCCN JONTXEXBTWSUKE-UHFFFAOYSA-N 0.000 description 1
XIZKIJKZPGHKKR-UHFFFAOYSA-N 2-[2-(2-chloro-2-oxoethoxy)ethoxy]acetyl chloride Chemical compound ClC(=O)COCCOCC(Cl)=O XIZKIJKZPGHKKR-UHFFFAOYSA-N 0.000 description 1
125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
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 1
229910010084 LiAlH4 Inorganic materials 0.000 description 1
238000005684 Liebig rearrangement reaction Methods 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
125000002947 alkylene group Chemical group 0.000 description 1
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
229910052786 argon Inorganic materials 0.000 description 1
238000010420 art technique Methods 0.000 description 1
230000008901 benefit Effects 0.000 description 1
239000013060 biological fluid Substances 0.000 description 1
150000001768 cations Chemical class 0.000 description 1
FITUNPSTVBUGAH-UHFFFAOYSA-N chloroform;heptane Chemical compound ClC(Cl)Cl.CCCCCCC FITUNPSTVBUGAH-UHFFFAOYSA-N 0.000 description 1
OQNGCCWBHLEQFN-UHFFFAOYSA-N chloroform;hexane Chemical compound ClC(Cl)Cl.CCCCCC OQNGCCWBHLEQFN-UHFFFAOYSA-N 0.000 description 1
125000000068 chlorophenyl group Chemical group 0.000 description 1
238000010668 complexation reaction Methods 0.000 description 1
229940125898 compound 5 Drugs 0.000 description 1
238000001816 cooling Methods 0.000 description 1
230000008878 coupling Effects 0.000 description 1
238000010168 coupling process Methods 0.000 description 1
238000005859 coupling reaction Methods 0.000 description 1
150000004985 diamines Chemical class 0.000 description 1
230000000694 effects Effects 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
229910001385 heavy metal Inorganic materials 0.000 description 1
125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
238000009533 lab test Methods 0.000 description 1
238000011031 large-scale manufacturing process Methods 0.000 description 1
239000003446 ligand Substances 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004998 naphthylethyl group Chemical group C1(=CC=CC2=CC=CC=C12)CC* 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
125000006501 nitrophenyl group Chemical group 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
239000002243 precursor Substances 0.000 description 1
238000000746 purification Methods 0.000 description 1
230000009467 reduction Effects 0.000 description 1
238000010992 reflux Methods 0.000 description 1
238000006798 ring closing metathesis reaction Methods 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
238000013341 scale-up Methods 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
239000000725 suspension Substances 0.000 description 1
230000002194 synthesizing effect Effects 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
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
125000003944 tolyl group Chemical group 0.000 description 1
230000007704 transition Effects 0.000 description 1
229910052723 transition metal Inorganic materials 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D273/00—Heterocyclic compounds containing rings having nitrogen and oxygen atoms as the only ring hetero atoms, not provided for by groups C07D261/00 - C07D271/00
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D291/00—Heterocyclic compounds containing rings having nitrogen, oxygen and sulfur atoms as the only ring hetero atoms
- C07D291/02—Heterocyclic compounds containing rings having nitrogen, oxygen and sulfur atoms as the only ring hetero atoms not condensed with other rings
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N27/00—Investigating or analysing materials by the use of electric, electrochemical, or magnetic means
- G01N27/26—Investigating or analysing materials by the use of electric, electrochemical, or magnetic means by investigating electrochemical variables; by using electrolysis or electrophoresis
- G01N27/28—Electrolytic cell components
- G01N27/30—Electrodes, e.g. test electrodes; Half-cells
- G01N27/333—Ion-selective electrodes or membranes
- G01N27/3335—Ion-selective electrodes or membranes the membrane containing at least one organic component

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Molecular Biology (AREA)
Chemical Kinetics & Catalysis (AREA)
Electrochemistry (AREA)
Physics & Mathematics (AREA)
Analytical Chemistry (AREA)
Biochemistry (AREA)
General Health & Medical Sciences (AREA)
General Physics & Mathematics (AREA)
Immunology (AREA)
Pathology (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

IL8806488A 1987-12-14 1988-10-17 Large scale synthesis of twelve member diazamonocyclic compounds and some such novel compounds IL88064A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US13274187A	1987-12-14	1987-12-14

Publications (2)

Publication Number	Publication Date
IL88064A0 IL88064A0 (en)	1989-06-30
IL88064A true IL88064A (en)	1994-02-27

Family

ID=22455391

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL8806488A IL88064A (en)	1987-12-14	1988-10-17	Large scale synthesis of twelve member diazamonocyclic compounds and some such novel compounds

Country Status (6)

Country	Link
EP (1)	EP0321199A3 (fr)
JP (1)	JPH01172389A (fr)
AU (1)	AU630077B2 (fr)
CA (1)	CA1323873C (fr)
DK (1)	DK693588A (fr)
IL (1)	IL88064A (fr)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IL84422A (en) *	1987-04-15	1993-03-15	Technicon Instr	Process for the preparation of chromogenic cryptahemispherands
CA2031735A1 (fr) *	1989-12-08	1991-06-09	Daljit S. Dhanoa	Inhibiteurs de renine cyclique, renfermant de l'acide 3(s)-amino-4-cyclohexyl-2(r)-hydroxybutanoique ou 4-cyclohexyl-(2r,3s)-dihydroxybutanoique, ou encore des analogues apparentes
US5132001A (en) *	1990-05-21	1992-07-21	Bakos Vincent W	Hemispherand ionophores having increased lipophilicity
WO2014097309A1 (fr)	2012-12-17	2014-06-26	Asian Paints Ltd.	Revêtement autonettoyant répondant à des stimuli

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3888877A (en) *	1969-06-11	1975-06-10	Schering Corp	Macrocyclic compounds and complexes thereof
US4156683A (en) *	1973-03-26	1979-05-29	Schering Corporation	Complexes of macrocyclic compounds
IL84422A (en) *	1987-04-15	1993-03-15	Technicon Instr	Process for the preparation of chromogenic cryptahemispherands

1988
- 1988-10-14 CA CA000580193A patent/CA1323873C/fr not_active Expired - Fee Related
- 1988-10-17 IL IL8806488A patent/IL88064A/en unknown
- 1988-11-08 AU AU24905/88A patent/AU630077B2/en not_active Ceased
- 1988-11-18 JP JP63290361A patent/JPH01172389A/ja active Pending
- 1988-12-13 DK DK693588A patent/DK693588A/da not_active Application Discontinuation
- 1988-12-14 EP EP88311810A patent/EP0321199A3/fr not_active Withdrawn

Also Published As

Publication number	Publication date
AU630077B2 (en)	1992-10-22
EP0321199A2 (fr)	1989-06-21
EP0321199A3 (fr)	1990-05-02
IL88064A0 (en)	1989-06-30
DK693588D0 (da)	1988-12-13
JPH01172389A (ja)	1989-07-07
CA1323873C (fr)	1993-11-02
AU2490588A (en)	1989-06-15
DK693588A (da)	1989-06-15

Publication	Publication Date	Title
CN115894329B (zh)	2023-08-18	一种轴手性含2-硫氰基-3-芳基的吲哚衍生物合成方法
SU1003758A3 (ru)	1983-03-07	Способ получени комплексных соединений щелочных металлов
US4983779A (en)	1991-01-08	Process for the preparation of vinyl ethers
US4900818A (en)	1990-02-13	Large scale synthesis of twelve member diazamonocyclic compounds
IL88064A (en)	1994-02-27	Large scale synthesis of twelve member diazamonocyclic compounds and some such novel compounds
DE69427278T2 (de)	2001-10-25	Asymmetrisches Epoxidationsverfahren unter Verwendung von optisch-aktiven Mangankomplexen
RU2073032C1 (ru)	1997-02-10	Способ получения полисульфидных полимеров и комплексные соединения гидросульфидов щелочных металлов или аммония с серой в качестве реагентов для осуществления этого способа
US4421923A (en)	1983-12-20	Ring substituted crown ethers and method of producing same
KR100369274B1 (ko)	2003-05-17	4-히드록시-2-피롤리돈의개량제법
CN112778189A (zh)	2021-05-11	（3r,4s）-n-取代基-3-羧酸-4-乙基吡咯烷、中间体及乌帕替尼
RU2242467C2 (ru)	2004-12-20	Способ получения производных тиобарбитуровой кислоты
EP4269387A1 (fr)	2023-11-01	Composé de pyrrolinone et procédé de synthèse associé
CN118600444B (zh)	2025-11-11	一种磷酰亚胺衍生物的电化学合成方法
KR850001065B1 (ko)	1985-07-25	1rs, 4sr, 5rs-4-(4, 8-디메틸-5-히드록시-7-논엔-1-일)-4-메틸-3, 8-디옥사비시클로[3.2.1] 옥탄-1-아세트산의 전합성방법
US4294970A (en)	1981-10-13	Oxidation of alpha-alkylated, benzyl-substituted 2-thiopyridine 1-oxides
US5300274A (en)	1994-04-05	Method for making molybdenum and sulfur containing compounds
Wang et al.	1999	An Efficient and Convenient Procedure for Preparation of Diaryl Carbazone from aryl substituted carbazide
DE69624531T2 (de)	2003-03-20	Substituierte Chinolinverbindungen als Zwischenverbindungen für Herbizide und Herstellungsverfahren
US3972922A (en)	1976-08-03	Process for preparing ether tricarboxylates
EP0282556A1 (fr)	1988-09-21	Procede de preparation de 3-(1-hydroxyalkyl)-5-5- diphenylhydantoine.
EP0190786B1 (fr)	1990-04-04	Dérivés de l'azétidine, procédé pour leur préparation, et leur utilisation comme produits intermédiaires
SE433747B (sv)	1984-06-12	Forfarande for framstellning av 3-amino-rifamycin s och sv
CN120398774A (zh)	2025-08-01	一种合成c-3取代的喹喔啉酮衍生物的方法
KR850001474B1 (ko)	1985-10-10	1-페닐-3(2,2-디알콕시)에틸-3,6-디아자헵탄-4,7-디온 유도체의 제조방법
KR860001087B1 (ko)	1986-08-07	7-아미노-3-(5-메틸-1,3,4-티아디아졸-2-일) 티오메틸-3-세펨-4-카르복실산의 제조방법