Acetyl chloride → Imiquimod hydrochloride

HRID 1920274노트

반응식

HRID 1920274 반응식
C([Cl:4])(=O)C.[NH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12]1[N:16]([CH2:17][CH:18]([CH3:20])[CH3:19])[CH:15]=[N:14][C:13]=1[C:21]#[N:22]>C(O)C>[ClH:4].[CH3:20][CH:18]([CH3:19])[CH2:17][N:16]1[C:12]2[C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=3[N:5]=[C:21]([NH2:22])[C:13]=2[N:14]=[CH:15]1

참가 물질

4

반응물 2

HCID 6367Acetyl chlorideHCID 251645955-(2-aminophenyl)-1-(2-methylpropyl)-1H-imidazole-4-carbonitrile

생성물 1

HCID 13982876Imiquimod hydrochloride수율 23.4%

시약·촉매·용매 1

HCID 702Ethanol용매2회

실험 절차

A solution of acetyl chloride (0.15 mL, 2 mmol) in ethanol (2 mL) was added to a solution of 5-(2-aminophenyl)-1-(2-methylpropyl)-1H-imidazole-4-carbonitrile (0.13 g) in ethanol (5 mL). The mixture was heated at reflux for two hours and allowed to cool to ambient temperature. The volume of the mixture was decreased to 2 mL by concentrating under reduced pressure. A solid was present, and the remaining liquid was decanted away from the solid, which was washed with diethyl ether (2×2 mL) and dried overnight in a vacuum oven at room temperature to provide 0.035 g (23% for Example 19 and Example 20 combined) of 1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-4-amine hydrochloride as a beige solid, mp>265° C.

후처리

  1. temperatureThe mixture was heated
  2. temperatureat reflux for two hours
  3. concentrationby concentrating under reduced pressure
  4. customthe remaining liquid was decanted away from the solid, which
  5. washwas washed with diethyl ether (2×2 mL)
  6. customdried overnight in a vacuum oven at room temperature

출처 및 근거

ORD 기록
ord-087d5ed3a94740e9abb0728479f19740
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08168802B2

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