Sodium Hydroxide → 2-amino-5-(3-(1-ethyl-1H-pyrazol-5-yl)-1H-pyrrolo(2,3-b)pyridin-5-yl)-N,N-dimethylbenzamide

HRID 2234671노트

반응식

HRID 2234671 반응식
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]3[C:16]([C:17]4[N:18]([CH2:22][CH3:23])[N:19]=[CH:20][CH:21]=4)=[CH:15][N:14](COC(=O)C(C)(C)C)[C:11]3=[N:12][CH:13]=2)=[CH:4][C:3]=1[C:32](=[O:36])[N:33]([CH3:35])[CH3:34].[OH-].[Na+].C(=O)(O)[O-].[Na+]>O1CCCC1.CO>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]3[C:16]([C:17]4[N:18]([CH2:22][CH3:23])[N:19]=[CH:20][CH:21]=4)=[CH:15][NH:14][C:11]3=[N:12][CH:13]=2)=[CH:4][C:3]=1[C:32]([N:33]([CH3:34])[CH3:35])=[O:36]

참가 물질

6

반응물 3

HCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 577315452,2-dimethyl-propionic acid 5-(4-amino-3-dimethylcarbamoyl-phenyl)-3-(2-ethyl-2H-pyrazol-3-yl)-pyrrolo[2,3-b]pyridin-1-ylmethyl ester

생성물 1

HCID 1355664332-amino-5-(3-(1-ethyl-1H-pyrazol-5-yl)-1H-pyrrolo(2,3-b)pyridin-5-yl)-N,N-dimethylbenzamide

시약·촉매·용매 2

HCID 887Methanol용매HCID 8028Tetrahydrofuran용매

실험 절차

2,2-dimethyl-propionic acid 5-(4-amino-3-dimethylcarbamoyl-phenyl)-3-(2-ethyl-2H-pyrazol-3-yl)-pyrrolo[2,3-b]pyridin-1-ylmethyl ester was dissolved in tetrahydrofuran. 1 M sodium hydroxide in methanol was added to the mixture, and the reaction was stirred for 2 h at room temperature until complete conversion was confirmed by HPLC-MS. Saturated aqueous sodium bicarbonate solution was added and the mixture extracted with dichloromethane. The organic layer was dried over sodium sulfate and concentrated. The crude material was purified by preparative HPLC to give 2-amino-5-[3-(2-ethyl-2H-pyrazol-3-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-N,N-dimethyl-benzamide. 1H-NMR (250 MHz, d6-DMSO) δ 12.12 (s, 1H), 8.51 (d, J=2.0 Hz, 1H), 7.97 (d, J=2.3 Hz, 1H), 7.76 (d, J=2.3 Hz, 1H), 7.55 (s, 1H), 7.47 (d, J=8.8 Hz, 1H), 7.35 (d, J=2.0 Hz, 1H), 6.82 (d, J=8.0 Hz, 1H), 6.53 (s, 1H), 5.29 (s, 2H), 4.20 (quart., J=7.3 Hz, 2H), 2.96 (s, 6H), 1.32 (t, J=7.1 Hz, 3H); MS: m/z 375.1 (M+H+).

후처리

  1. extractionthe mixture extracted with dichloromethane
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. concentrationconcentrated
  4. customThe crude material was purified by preparative HPLC

출처 및 근거

ORD 기록
ord-53c7d09ba481425bafde8079ec189c72
출처 데이터셋
uspto-grants-2010_05
특허 번호
US07709645B2

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