Triethylamine → HCID 16224282、化合物

HRID 1930098ノート

反応式

HRID 1930098 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][CH3:38])=[O:35]>CN(C)C=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][CH3:38])[C:18]=2[N:19]=1)[CH3:32]

参加物

5

反応物 3

HCID 8471Triethylamine2 回HCID 10928Ethyl chloroformate2 回HCID 10309114CPG-52852

生成物 1

HCID 16224282HCID 16224282、化合物収率 68%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

Triethylamine (3.86 mL, 10 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 N,N-dimethylformamide (DMF) (10 mL). Ethyl chloroformate (1.5 g, 5 eq) was added dropwise to give a clear solution. The reaction mixture was allowed to come to ambient temperature with stirring for 2 hours. Additional triethylamine (3.86 mL, 10 eq) and ethyl chloroformate (3.86 mL, 10 eq) were added and the reaction mixture was stirred overnight. The reaction mixture was poured onto crushed ice 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, 2500 mL) followed by recrystallization from acetonitrile to provide 0.815 g of ethyl 2-ethyl-1-{4-[(methylsulfonyl)amino]butyl}-1H-imidazo[4,5-c]quinolin-4-ylcarbamate as a white crystalline solid, mp 185-187° C. Anal calcd for C20H27N5O4S: C, 55.41; H, 6.28; N, 16.15. Found: C, 55.30; H, 6.29; N, 16.24.

後処理

  1. temperaturea chilled
  2. customto give a clear solution
  3. customto come to ambient temperature
  4. stirringthe reaction mixture was stirred overnight
  5. additionThe reaction mixture was poured
  6. customonto crushed ice
  7. extractionextracted with dichloromethane (50 mL)
  8. washThe organic layer was washed sequentially with water (2×50 mL), 4% sodium carbonate (50 mL), water (50 mL), and brine (50 mL)
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by automated flash chromatography (silica gel
  11. washeluted with a linear gradient of 0-25% CMA in chloroform
  12. custom2500 mL) followed by recrystallization from acetonitrile

出典と根拠

ORDレコード
ord-b3a2a515971a4b6bb7b165734e058007
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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