Sodium Hydroxide → HCID 178484417, compound

HRID 2388978Notes

Reaction equation

HRID 2388978 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:43]=[CH:44][CH:45]=1)[CH2:5][C:6]1[C:14]2[C:9](=[N:10][CH:11]=[C:12]([C:15]3[CH:20]=[CH:19][C:18]([NH:21][C:22]([N:24]4[CH2:29][CH2:28][O:27][CH2:26][CH2:25]4)=[O:23])=[C:17]([C:30](=[O:34])[N:31]([CH3:33])[CH3:32])[CH:16]=3)[CH:13]=2)[N:8](COC(=O)C(C)(C)C)[N:7]=1.[OH-].[Na+]>O1CCCC1.CO>[Cl:1][C:2]1[CH:3]=[C:4]([CH:43]=[CH:44][CH:45]=1)[CH2:5][C:6]1[C:14]2[C:9](=[N:10][CH:11]=[C:12]([C:15]3[CH:20]=[CH:19][C:18]([NH:21][C:22]([N:24]4[CH2:25][CH2:26][O:27][CH2:28][CH2:29]4)=[O:23])=[C:17]([C:30](=[O:34])[N:31]([CH3:32])[CH3:33])[CH:16]=3)[CH:13]=2)[NH:8][N:7]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 68662423HCID 68662423, compound

Product 1

HCID 178484417HCID 178484417, compoundYield 12.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

2,2-Dimethyl-propionic acid 3-(3-chloro-benzyl)-5-{3-dimethylcarbamoyl-4-[(morpholine-4-carbonyl)-amino]-phenyl}-pyrazolo[3,4-b]pyridin-1-ylmethyl ester (180 mg, 0.284 mmol) was dissolved in tetrahydrofuran (10 ml). 1 M sodium hydroxide in methanol (3.0 ml) 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 18 mg (12%) of morpholine-4-carboxylic acid {4-[3-(3-chloro-benzyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]-2-dimethylcarbamoyl-phenyl}-amide. 1H-NMR (250 MHz, DMSO-d6) δ 13.48 (s, 1H), 8.82 (d, J=2.0 Hz, 1H), 8.77 (s, 1H), 8.46 (d, J=2.0 Hz, 1H), 7.79-7.71 (m, 2H), 7.64 (s, 1H), 7.47 (s, 1H), 7.34-7.20 (m, 3H), 4.35 (s, 2H), 3.66-3.56 (m, 4H), 3.43-3.35 (m, 4H), 2.98 (s, 6H); MS: m/z 519.2 (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-0dbcbbf665f549d2aee0a5d3b56cb0e9
Source dataset
uspto-grants-2012_09
Patent number
US08268994B2

Reaction notes

Loading…