SU566842A1 - Method of preparing substituted imidazopyridines - Google Patents
Method of preparing substituted imidazopyridinesInfo
- Publication number
- SU566842A1 SU566842A1 SU7602310356A SU2310356A SU566842A1 SU 566842 A1 SU566842 A1 SU 566842A1 SU 7602310356 A SU7602310356 A SU 7602310356A SU 2310356 A SU2310356 A SU 2310356A SU 566842 A1 SU566842 A1 SU 566842A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- preparing substituted
- substituted imidazopyridines
- imidazopyridines
- pyridip
- imidazo
- Prior art date
Links
- 150000005232 imidazopyridines Chemical class 0.000 title 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 2
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- -1 4 - dimethylaminophenyl Chemical group 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- OYTKINVCDFNREN-UHFFFAOYSA-N amifampridine Chemical compound NC1=CC=NC=C1N OYTKINVCDFNREN-UHFFFAOYSA-N 0.000 description 1
- 229960004012 amifampridine Drugs 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
Landscapes
- Nitrogen Condensed Heterocyclic Rings (AREA)
Description
Пример 1. Получение 2-фенилимидазо 4,5-с пиридина (соединение № 1).Example 1. The preparation of 2-phenylimidazo 4,5-c pyridine (compound No. 1).
Смесь, состо вшую из эквимолекул рных количеств 3,4-диаминопиридина, бензальдегида и серы, нагревают 4 ч ири 170-175°С, охлаждают до комнатной темиературы и продукт реакции кристаллизуют из водного спирта. Т. пл. 227°С. Выход 91%.A mixture consisting of equimolecular amounts of 3,4-diaminopyridine, benzaldehyde and sulfur is heated for 4 hours with 170-175 ° C, cooled to room temperature and the reaction product is crystallized from aqueous alcohol. T. pl. 227 ° C. Yield 91%.
В случае проведени реакции в растворителе (мезитилен) на 1 вес. ч. серы берут 25 вес. ч. мезитилена. Реакцию провод т при температуре кипепи реакционной массы 2-4 ч. Осадок после охлаждени отфильтровывают и очищают кристаллизацией.If the reaction is carried out in a solvent (mesitylene) by 1 weight. h. sulfur take 25 weight. h. mesitylene. The reaction is carried out at the boiling point of the reaction mass for 2-4 hours. After cooling, the precipitate is filtered off and purified by crystallization.
Аналогично примеру 1 с использованием соответствующих исходных продуктов при нагревании в течение 1-6 ч при 150-175°С получены следующие целевые соединени :Analogously to Example 1, using the corresponding starting materials, the following target compounds were obtained by heating for 1-6 hours at 150-175 ° C:
№22- (4 - диметиламинофенил) -имидазо 4,5-с пиридип;No. 22- (4 - dimethylaminophenyl) -imidazo 4,5-c pyridip;
№ 3 2 - (4-метоксифенил)-имидазо 4,5-с пиридин;No. 3 2- (4-methoxyphenyl) -imidazo 4,5-c pyridine;
№ 4 1 - метил-2-(1-метилиндолил-2)-имидазо 4 ,5-Ь пиридип;No. 4 1 - methyl-2- (1-methylindolyl-2) -imidazo 4, 5-b pyridip;
№ 5 2 - фенилимидазо 4,5-Ь пиридип;No. 5 2 - phenylimidazo 4,5-b pyridip;
№ 6 2 - 4-(диметиламино)-фенил -5-хлоримидазо 4,5-& пиридин.No. 6 2 - 4- (dimethylamino) -phenyl-5-chlorimidazo 4,5- & pyridine.
Свойства полученных соединений приведены в таблице.Properties of the compounds obtained are shown in the table.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU7602310356A SU566842A1 (en) | 1976-01-06 | 1976-01-06 | Method of preparing substituted imidazopyridines |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU7602310356A SU566842A1 (en) | 1976-01-06 | 1976-01-06 | Method of preparing substituted imidazopyridines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU566842A1 true SU566842A1 (en) | 1977-07-30 |
Family
ID=20644302
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU7602310356A SU566842A1 (en) | 1976-01-06 | 1976-01-06 | Method of preparing substituted imidazopyridines |
Country Status (1)
| Country | Link |
|---|---|
| SU (1) | SU566842A1 (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4603139A (en) * | 1981-11-10 | 1986-07-29 | Burroughs Wellcome Co. | Bicycle compounds, processes for their preparation and pharmaceutical formulations containing compounds |
| US4616090A (en) * | 1981-08-19 | 1986-10-07 | Merck Patent Gesellschaft Mit Beschrankter Haftung | 2-arylimidazopyridines intermediates |
| RU2400482C2 (en) * | 2006-01-16 | 2010-09-27 | Н.В. Органон | 6-PHENYL-1H-IMIDAZO[4,5-c]PYRIDINE-4-CARBONITRILE DERIVATIVES AS CATEPSIN K AND S INHIBITORS |
| RU2498984C2 (en) * | 2007-09-12 | 2013-11-20 | Сентр Насьональ Де Ла Решерш Сьентифик | Perharidines as cdk inihibitors |
-
1976
- 1976-01-06 SU SU7602310356A patent/SU566842A1/en active
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4616090A (en) * | 1981-08-19 | 1986-10-07 | Merck Patent Gesellschaft Mit Beschrankter Haftung | 2-arylimidazopyridines intermediates |
| US5104881A (en) * | 1981-08-19 | 1992-04-14 | Merck Patent Gesellschaft Mit Beschrankter Haftung | 2-arylimidazopyridines |
| US4603139A (en) * | 1981-11-10 | 1986-07-29 | Burroughs Wellcome Co. | Bicycle compounds, processes for their preparation and pharmaceutical formulations containing compounds |
| RU2400482C2 (en) * | 2006-01-16 | 2010-09-27 | Н.В. Органон | 6-PHENYL-1H-IMIDAZO[4,5-c]PYRIDINE-4-CARBONITRILE DERIVATIVES AS CATEPSIN K AND S INHIBITORS |
| RU2498984C2 (en) * | 2007-09-12 | 2013-11-20 | Сентр Насьональ Де Ла Решерш Сьентифик | Perharidines as cdk inihibitors |
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