Propyl Isothiocyanate → N-[4-(4-amino-2-phenyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-N'-propylthiourea

HRID 1263506

반응식

HRID 1263506 반응식
[CH2:1]([N:4]=[C:5]=[S:6])[CH2:2][CH3:3].[NH2:7][CH2:8][CH2:9][CH2:10][CH2:11][N:12]1[C:24]2[C:23]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[N:17]=[C:16]([NH2:25])[C:15]=2[N:14]=[C:13]1[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C(Cl)(Cl)Cl.N1C=CC=CC=1>[NH2:25][C:16]1[C:15]2[N:14]=[C:13]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[N:12]([CH2:11][CH2:10][CH2:9][CH2:8][NH:7][C:5]([NH:4][CH2:1][CH2:2][CH3:3])=[S:6])[C:24]=2[C:23]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[N:17]=1

참가 물질

5

반응물 2

HCID 69403Propyl IsothiocyanateHCID 121489921-(4-aminobutyl)-2-phenyl-1H-imidazo[4,5-c]quinolin-4-amine

생성물 1

HCID 9954525N-[4-(4-amino-2-phenyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-N'-propylthiourea수율 6.6%

시약·촉매·용매 2

HCID 1049Pyridine용매HCID 6212Chloroform용매2회

실험 절차

A solution of propyl isothiocyanate (0.78 g, 7.72 mmol) in chloroform (5 mL) was added at ambient temperature to a solution of 1-(4-aminobutyl)-2-phenyl-1H-imidazo[4,5-c]quinolin-4-amine (0.256 g, 7.72 mmol) in a mixture of chloroform (25 mL) and pyridine (5 mL). The reaction mixture was maintained at ambient temperature over the weekend. The reaction was quenched with ethanol and then concentrated under vacuum to provide a pale orange syrup. This material was purified by flash chromatography (silica gel, eluting with 10% methanol in dichloromethane). The pure fractions were combined and concentrated under vacuum to provide 0.22 g of N-[4-(4-amino-2-phenyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-N′-propylthiourea as a white solid, m.p. 113-116° C. Mass spec M+1=433.2.

후처리

  1. customThe reaction was quenched with ethanol
  2. concentrationconcentrated under vacuum
  3. customto provide a pale orange syrup
  4. customThis material was purified by flash chromatography (silica gel, eluting with 10% methanol in dichloromethane)
  5. concentrationconcentrated under vacuum

출처 및 근거

ORD 기록
ord-99b463b27ac349488a37bc4948c587fc
출처 데이터셋
uspto-grants-2003_04
특허 번호
US06541485B1

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