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

HRID 1837020ノート

反応式

HRID 1837020 の反応式
[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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 1049Pyridine溶媒HCID 6212Chloroform溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-83fb98a51a7245c0b4897489dc00e19c
出典データセット
uspto-grants-2004_08
特許番号
US06780873B2

反応ノート

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