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

HRID 531599Notes

Reaction equation

HRID 531599 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:43]=[C:44]([F:46])[CH:45]=1)[CH2:5][N:6]1[CH:10]=[C:9]([C:11]2[C:19]3[C:14](=[N:15][CH:16]=[C:17]([C:20]4[CH:25]=[CH:24][C:23]([NH:26][S:27]([CH3:30])(=[O:29])=[O:28])=[C:22]([O:31][CH3:32])[CH:21]=4)[CH:18]=3)[N:13](S(C3C=CC(C)=CC=3)(=O)=O)[CH:12]=2)[CH:8]=[N:7]1.[OH-].[Li+]>C1COCC1.CO.O>[F:46][C:44]1[CH:43]=[C:4]([CH:3]=[C:2]([F:1])[CH:45]=1)[CH2:5][N:6]1[CH:10]=[C:9]([C:11]2[C:19]3[C:14](=[N:15][CH:16]=[C:17]([C:20]4[CH:25]=[CH:24][C:23]([NH:26][S:27]([CH3:30])(=[O:29])=[O:28])=[C:22]([O:31][CH3:32])[CH:21]=4)[CH:18]=3)[NH:13][CH:12]=2)[CH:8]=[N:7]1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 90031517N-(4-(3-(1-(3,5-difluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-methoxyphenyl)methane sulfonamide

Product 1

HCID 72944325N-(4-(3-(1-(3,5-difluorobenzyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-methoxy phenyl)methanesulfonamideYield 53.3%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

Using similar reaction conditions as described in step-iii of example-1, N-(4-(3-(1-(3,5-difluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-methoxyphenyl)methane sulfonamide (95 mg, 0.14 mmol) was hydrolyzed by lithium hydroxide (18 mg, 0.42 mmol) in THF/methanol/water (2/2/1 ml) to yield 38 mg (52.1% yield) of the titled compound after purification by preparative TLC (Silicagel-1000 micron) using 5% methanol in chloroform as eluent. 1H NMR (DMSO-d6, 300 MHz): δ 11.8 (s, 1H), 8.95 (s, 1H), 8.559-8.552 (d, 1H), 8.42 (s, 1H), 8.367-8.361 (d, 1H), 7.99 (s, 1H), 7.77-7.76 (d, 1H), 7.38 (s, 1H), 7.35-7.32 (m, 2H), 7.20-7.10 (m, 1H), 6.97-6.95 (d, 2H), 5.39 (s, 2H), 3.94 (s, 3H), 2.96 (s, 3H). MS: m/z=510.1 (M+1), HPLC: 87.42% in method B.

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-2cd0980c77f0485fa5de363af9a80802
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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