Sodium Hydroxide → HCID 178484418, compound

HRID 2388983Notes

Reaction equation

HRID 2388983 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]3[C:16]([CH2:17][C:18]4[CH:23]=[CH:22][C:21]([N:24]([CH3:26])[CH3:25])=[CH:20][CH:19]=4)=[N:15][N:14](COC(=O)C(C)(C)C)[C:11]3=[N:12][CH:13]=2)=[CH:4][C:3]=1[C:35](=[O:39])[N:36]([CH3:38])[CH3:37].[OH-].[Na+]>O1CCCC1.CO>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]3[C:16]([CH2:17][C:18]4[CH:19]=[CH:20][C:21]([N:24]([CH3:25])[CH3:26])=[CH:22][CH:23]=4)=[N:15][NH:14][C:11]3=[N:12][CH:13]=2)=[CH:4][C:3]=1[C:35]([N:36]([CH3:37])[CH3:38])=[O:39]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 68662665HCID 68662665, compound

Product 1

HCID 178484418HCID 178484418, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

2,2-Dimethyl-propionic acid 5-(4-amino-3-dimethylcarbamoyl-phenyl)-3-(4-dimethylamino-benzyl)-pyrazolo[3,4-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 hours at room temperature. The reaction was quenched with sodium bicarbonate solution and extracted with dichloromethane. The organic layer was dried, filtered, and concentrated. The crude material was purified by mass-triggered reverse-phase HPLC to give 2-amino-5-[3-(4-dimethylamino-benzyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]-N,N-dimethyl-benzamide. 1H-NMR (250 MHz, DMSO-d6) δ 13.24 (s, 1H), 8.67 (d, J=2.3 Hz, 1H), 8.06 (d, J=2.3 Hz, 1H), 7.43 (dd, J=8.5, 2.3 Hz, 1H), 7.30 (d, J=2.0 Hz, 1H), 7.18 (d, J=8.8 Hz, 2H), 6.80 (d, J=8.5 Hz, 1H), 6.64 (d, J=8.8 Hz, 2H), 5.34 (s, 2H), 4.17 (s, 2H), 2.96 (s, 6H), 2.81 (s, 6H). MS: m/z 415.5 (M+H+).

Workup

  1. customThe reaction was quenched with sodium bicarbonate solution
  2. extractionextracted with dichloromethane
  3. customThe organic layer was dried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude material was purified by mass-triggered reverse-phase HPLC

Sources & evidence

ORD record
ord-b429d2846c664af2a94ee891cf71d217
Source dataset
uspto-grants-2012_09
Patent number
US08268994B2

Reaction notes

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