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

HRID 2234671ノート

反応式

HRID 2234671 の反応式
[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]

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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+).

後処理

  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

出典と根拠

ORDレコード
ord-53c7d09ba481425bafde8079ec189c72
出典データセット
uspto-grants-2010_05
特許番号
US07709645B2

反応ノート

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