5-Aminoimidazole-4-carboxamide hydrochloride → 4-(3-Chlorophenyl)imidazo[1,5-a]pyrimidine-8-carboxamide

HRID 1199942

반응식

HRID 1199942 반응식
Cl.[NH2:2][C:3]1[N:4]=[CH:5][NH:6][C:7]=1[C:8]([NH2:10])=[O:9].[Cl:11][C:12]1[CH:13]=[C:14]([C:18](=O)[CH:19]=[CH:20]N(C)C)[CH:15]=[CH:16][CH:17]=1.C(=O)(O)[O-].[Na+]>C(O)(=O)C>[Cl:11][C:12]1[CH:13]=[C:14]([C:18]2[N:4]3[CH:5]=[N:6][C:7]([C:8]([NH2:10])=[O:9])=[C:3]3[N:2]=[CH:20][CH:19]=2)[CH:15]=[CH:16][CH:17]=1

참가 물질

5

반응물 3

HCID 661465-Aminoimidazole-4-carboxamide hydrochlorideHCID 516892Sodium BicarbonateHCID 7300651-(3-Chlorophenyl)-3-(dimethylamino)-2-propen-1-one

생성물 1

HCID 146774724-(3-Chlorophenyl)imidazo[1,5-a]pyrimidine-8-carboxamide수율 43.7%

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

A mixture of 13.9 g of 4-amino-5-imidazolecarboxamide hydrochloride, 24.0 g of 3'-chloro-3-dimethylaminoacrylophenone (U.S. Pat. No. 4,209,621, Ex. 50) and 200 ml of glacial acetic acid was heated at reflux for 5 hours. The liquid was evaporated in vacuo to give a yellow solid. The excess acid was neutralized with saturated sodium bicarbonate solution and this mixture was filtered and the solid was washed with water and then was dried. Recrystallization from ethanol-methanol gave 10.2 g of the desired product as yellow crystals, mp 252°-254° C.

후처리

  1. temperatureat reflux for 5 hours
  2. customThe liquid was evaporated in vacuo
  3. customto give a yellow solid
  4. filtrationthis mixture was filtered
  5. washthe solid was washed with water
  6. customwas dried
  7. customRecrystallization from ethanol-methanol

출처 및 근거

ORD 기록
ord-88695e327f1548d1979f4beef7f931dc
출처 데이터셋
uspto-grants-1990_02
특허 번호
US04904658

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