Propyl chloroformate → HCID 16224285、化合物

HRID 1930099ノート

反応式

HRID 1930099 の反応式
C(N(CC)CC)C.[NH2:8][C:9]1[C:18]2[N:19]=[C:20]([CH2:31][CH3:32])[N:21]([CH2:22][CH2:23][CH2:24][CH2:25][NH:26][S:27]([CH3:30])(=[O:29])=[O:28])[C:17]=2[C:16]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[N:10]=1.Cl[C:34]([O:36][CH2:37][CH2:38][CH3:39])=[O:35]>CN1C(=O)CCC1.O>[CH2:31]([C:20]1[N:21]([CH2:22][CH2:23][CH2:24][CH2:25][NH:26][S:27]([CH3:30])(=[O:29])=[O:28])[C:17]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=[C:9]([NH:8][C:34](=[O:35])[O:36][CH2:37][CH2:38][CH3:39])[C:18]=2[N:19]=1)[CH3:32]

参加物

6

反応物 3

HCID 7998Propyl chloroformateHCID 8471TriethylamineHCID 10309114CPG-52852

生成物 1

HCID 16224285HCID 16224285、化合物収率 34.5%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 13387N-methyl-2-pyrrolidone溶媒

実験手順

Triethylamine (1.93 mL, 5 eq) was added to a chilled (ice/water bath) suspension of N-[4-(4-amino-2-ethyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]methanesulfonamide (1.0 g, 1 eq) in NMP (6.0 mL). Propyl chloroformate (1.02 g, 3 eq) was added dropwise. The reaction mixture was allowed to come to ambient temperature and stirred for 24 hours. The reaction mixture was diluted with cold water (25 mL) and then extracted with dichloromethane (50 mL). The organic layer was washed sequentially with water (2×50 mL), 4% sodium carbonate (50 mL), water (50 mL), and brine (50 mL) and then concentrated under reduced pressure. The residue was purified by automated flash chromatography (silica gel eluted with a linear gradient of 0-25% CMA in chloroform, 2000 mL) followed by recrystallization from acetonitrile to provide 0.427 g of propyl 2-ethyl-1-{4-[(methylsulfonyl)amino]butyl}-1H-imidazo[4,5-c]quinolin-4-ylcarbamate as a white solid, mp 155-157° C. Anal calcd for C21H29N5O4S: C, 56.36; H, 6.53; N, 15.65. Found: C, 56.37; H, 6.37; N, 15.70.

後処理

  1. temperaturea chilled
  2. customto come to ambient temperature
  3. extractionextracted with dichloromethane (50 mL)
  4. washThe organic layer was washed sequentially with water (2×50 mL), 4% sodium carbonate (50 mL), water (50 mL), and brine (50 mL)
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by automated flash chromatography (silica gel
  7. washeluted with a linear gradient of 0-25% CMA in chloroform
  8. custom2000 mL) followed by recrystallization from acetonitrile

出典と根拠

ORDレコード
ord-2cf2ee8d8f94436fa8d7c74a71033b7f
出典データセット
uspto-grants-2012_05
特許番号
US08188111B2

反応ノート

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