Methyl chloroformate → HCID 178501950, 화합물

HRID 2388990노트

반응식

HRID 2388990 반응식
Cl[C:2]([O:4][CH3:5])=[O:3].[NH2:6][C:7]1[CH:17]=[CH:16][C:15]([C:18]2[CH:19]=[C:20]3[C:26]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=4[O:33][CH3:34])=[N:25][NH:24][C:21]3=[N:22][CH:23]=2)=[CH:14][C:8]=1[C:9]([N:11]([CH3:13])[CH3:12])=[O:10]>ClCCl>[CH3:5][O:4][C:2](=[O:3])[NH:6][C:7]1[CH:17]=[CH:16][C:15]([C:18]2[CH:19]=[C:20]3[C:26]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=4[O:33][CH3:34])=[N:25][NH:24][C:21]3=[N:22][CH:23]=2)=[CH:14][C:8]=1[C:9](=[O:10])[N:11]([CH3:13])[CH3:12]

참가 물질

4

반응물 2

HCID 6586Methyl chloroformateHCID 178489397HCID 178489397, 화합물

생성물 1

HCID 178501950HCID 178501950, 화합물수율 22%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Methyl chloroformate (42 ul, 0.53 mmol) was added dropwise to a solution of 2-amino-5-[3-(2-methoxy-phenyl)-1H-pyrazolo[3,4,b]pyridin-5-yl]-N,N-dimethyl-benzamide (21 mg, 0.05 mmol) in dichloromethane/saturated aqueous sodium bicarbonate (1:1) at 0° C. The mixture was stirred for another 3 hours, allowing to slowly warm to room temperature. The reaction was washed three times with water (5 ml), dried over sodium sulfate and concentrated to dryness. The crude was purified by flash chromatography on silica gel using a gradient of ethyl acetate and hexane to afford {2-dimethylcarbamoyl-4[3-(2-methoxy-phenyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]-phenyl}-carbamic acid methyl ester (4.9 mg, 21% yield). 1H NMR (500 MHz, DMSO-d6) δ 2.88 (d, 6H), 3.58 (s, 3H), 3.77 (s, 3H), 7.03 (m, 1H), 7.15 (d, 1H), 7.40 (m, 1H), 7.58 (s, 1H), 7.64 (d, 1H), 7.73 (d, 1H), 8.27 (s, 1H), 8.78 (s, 1H), 9.03 (s, 1H). 13.75 (s, 1H); MS: m/z 446.1 (M+H+).

후처리

  1. washThe reaction was washed three times with water (5 ml)
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated to dryness
  4. customThe crude was purified by flash chromatography on silica gel using a gradient of ethyl acetate and hexane

출처 및 근거

ORD 기록
ord-209b96ac35bb48f5a08a3a54c4980350
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08268994B2

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