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

HRID 1925458노트

반응식

HRID 1925458 반응식
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

참가 물질

5

반응물 3

HCID 222Ammonia2회HCID 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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매2회

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온도
170 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-0c85062f5a234a9c9df7a4b61ce1f9a8
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08178677B2

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