Lithium Hydroxide → N-(3-(3-(1-(2,5-difluorobenzyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl) methanesulfonamide

HRID 531474Notes

Reaction equation

HRID 531474 reaction equation
[F:1][C:2]1[CH:43]=[CH:42][C:41]([F:44])=[CH:40][C:3]=1[CH2:4][N:5]1[CH:9]=[C:8]([C:10]2[C:18]3[C:13](=[N:14][CH:15]=[C:16]([C:19]4[CH:20]=[C:21]([NH:25][S:26]([CH3:29])(=[O:28])=[O:27])[CH:22]=[CH:23][CH:24]=4)[CH:17]=3)[N:12](S(C3C=CC(C)=CC=3)(=O)=O)[CH:11]=2)[CH:7]=[N:6]1.[OH-].[Li+]>C1COCC1.O.CO>[F:1][C:2]1[CH:43]=[CH:42][C:41]([F:44])=[CH:40][C:3]=1[CH2:4][N:5]1[CH:9]=[C:8]([C:10]2[C:18]3[C:13](=[N:14][CH:15]=[C:16]([C:19]4[CH:20]=[C:21]([NH:25][S:26]([CH3:29])(=[O:27])=[O:28])[CH:22]=[CH:23][CH:24]=4)[CH:17]=3)[NH:12][CH:11]=2)[CH:7]=[N:6]1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 118523949N-(3-(3-(1-(2,5-difluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl) methanesulfonamide

Product 1

HCID 72944749N-(3-(3-(1-(2,5-difluorobenzyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl) methanesulfonamideYield 90.9%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

Using similar reaction conditions as described in step-iii of example-1, N-(3-(3-(1-(2,5-difluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl) methanesulfonamide (250 mg, 0.39 mmol) was hydrolyzed with lithium hydroxide (66 mg, 1.57 mmol) in THF/water/methanol (5/4/3 ml) mixture to afford 170 mg (89.94% yield) of the pure product. 1H NMR (DMSO-d6, 300 MHz): δ 11.83 (s, 1H), 8.47-8.32 (m, 3H), 7.97 (s, 1H), 7.799-7.794 (d, 1H), 7.64-7.55 (m, 3H), 7.49-7.44 (m, 3H), 7.32-7.21 (m, 2H), 5.44 (s, 2H), 3.03 (s, 3H) MS: m/z=479.8 (M+1), HPLC: 73.14% in method A.

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-c9d64063e168412f94bfecc430d4b763
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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