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

HRID 531591Notes

Reaction equation

HRID 531591 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]=[CH:9][C:8]([C:11]2[C:19]3[C:14](=[N:15][CH:16]=[C:17]([C:20]4[CH:21]=[CH:22][C:23]([O:31][CH3:32])=[C:24]([NH:26][S:27]([CH3:30])(=[O:29])=[O:28])[CH:25]=4)[CH:18]=3)[N:13](S(C3C=CC(C)=CC=3)(=O)=O)[CH:12]=2)=[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]=[CH:9][C:8]([C:11]2[C:19]3[C:14](=[N:15][CH:16]=[C:17]([C:20]4[CH:21]=[CH:22][C:23]([O:31][CH3:32])=[C:24]([NH:26][S:27]([CH3:30])(=[O:28])=[O:29])[CH:25]=4)[CH:18]=3)[NH:13][CH:12]=2)=[N:7]1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 90030829N-(5-(3-(1-(3,5-difluorobenzyl)-1H-pyrazol-3-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-methoxyphenyl) methane sulfonamide

Product 1

HCID 136274723N-(5-(3-(1-(3,5-difluorobenzyl)-1H-pyrazol-3-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-methoxy phenyl)methanesulfonamideYield 49.1%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

Using similar reaction conditions as described in step-iii of example-1, N-(5-(3-(1-(3,5-difluorobenzyl)-1H-pyrazol-3-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-methoxyphenyl) methane sulfonamide (53 mg, 0.0799 mmol) was hydrolyzed by lithium hydroxide (17 mg, 0.399 mmol) in THF/methanol/water (2/2/1 ml) to yield 20 mg of the titled compound. 1H NMR (DMSO-d6, 300 MHz): δ 11.8 (s, 1H), 9.00 (s, 1H), 8.538-8.530 (d, 1H), 8.45-8.44 (d, 1H), 7.89-7.88 (d, 2H), 7.55-7.54 (d, 1H), 7.50-7.46 (dd, 1H), 7.19-7.15 (m, 2H), 7.00-6.98 (m, 2H), 6.699-6.692 (d, 1H), 5.40 (s, 2H), 3.86 (s, 3H), 2.97 (s, 3H). MS: m/z=510.1 (M+1), HPLC: 96.47% in method B.

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-dced18df11d64e87af28f54aa49a2c44
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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