Ammonia → N-{2-[4-amino-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl]-1,1-dimethylethyl}methanesulfonamide

HRID 81883ノート

反応式

HRID 81883 の反応式
Cl[C:2]1[C:11]([NH:12][C:13](=O)[CH2:14][CH2:15][O:16][CH3:17])=[C:10]([NH:19][CH2:20][C:21]([NH:24][S:25]([CH3:28])(=[O:27])=[O:26])([CH3:23])[CH3:22])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.N.ClC1C(NC(=O)CCOC)=C(CC(NS(C)(=O)=O)(C)C)C2C(=CC=CC=2)[N:32]=1>CO>[NH2:32][C:2]1[C:11]2[N:12]=[C:13]([CH2:14][CH2:15][O:16][CH3:17])[N:19]([CH2:20][C:21]([NH:24][S:25]([CH3:28])(=[O:27])=[O:26])([CH3:22])[CH3:23])[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1

参加物

5

反応物 3

HCID 222Ammonia2 回HCID 86626601N-{2-chloro-4-[2-(methanesulfonylamino)-2-methylpropyl]aminoquinolin-3-yl}-3-methoxypropionamideHCID 86626602N-{2-chloro-4-[2-(methanesulfonylamino)-2-methylpropyl]quinolin-3-yl}-3-methoxypropionamide

生成物 1

HCID 10000533N-{2-[4-amino-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl]-1,1-dimethylethyl}methanesulfonamide収率 167.2%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒2 回

反応条件

温度
170 °C

実験手順

A Parr bomb was charged with 25.0 g of N-{2-chloro-4-[2-(methanesulfonylamino)-2-methylpropyl]aminoquinolin-3-yl}-3-methoxypropionamide and ammonia in methanol (300 mL of 7 N). A second vessel was charged with 30.21 g of N-{2-chloro-4-[2-(methanesulfonylamino)-2-methylpropyl]quinolin-3-yl}-3-methoxypropionamide and ammonia in methanol (400 mL of 7 N). Both vessels were sealed and then heated at 170° C. for 14 hours. The reaction mixtures were combined and the solvent was removed under reduced pressure. The residue was partitioned between dichloromethane and saturated aqueous sodium bicarbonate. The organic layer was washed sequentially with saturated aqueous sodium bicarbonate and brine, dried over sodium sulfate, filtered, and then concentrated under reduced pressure to provide 38.16 g of N-{2-[4-amino-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl]-1,1-dimethylethyl}methanesulfonamide as an off white foam.

後処理

  1. customBoth vessels were sealed
  2. customThe reaction mixtures
  3. customthe solvent was removed under reduced pressure
  4. customThe residue was partitioned between dichloromethane and saturated aqueous sodium bicarbonate
  5. washThe organic layer was washed sequentially with saturated aqueous sodium bicarbonate and brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-f442abd5d9ae46e8b46ebdf2f73ebd2c
出典データセット
uspto-grants-2014_09
特許番号
US08846710B2

反応ノート

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