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

HRID 531593Notes

Reaction equation

HRID 531593 reaction equation
[F:1][C:2]1[CH:45]=[CH:44][C:43]([F:46])=[CH:42][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]=[CH:21][C:22]([O:30][CH3:31])=[C:23]([NH:25][S:26]([CH3:29])(=[O:28])=[O:27])[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.CO.O>[F:1][C:2]1[CH:45]=[CH:44][C:43]([F:46])=[CH:42][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]=[CH:21][C:22]([O:30][CH3:31])=[C:23]([NH:25][S:26]([CH3:29])(=[O:28])=[O:27])[CH:24]=4)[CH:17]=3)[NH:12][CH:11]=2)[CH:7]=[N:6]1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 90030463N-(5-(3-(1-(2,5-difluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-methoxyphenyl)methanesulfonamide

Product 1

HCID 72944103N-(5-(3-(1-(2,5-difluorobenzyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-methoxyphenyl)methanesulfonamideYield 22.9%

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-(2,5-difluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-methoxyphenyl)methanesulfonamide (120 mg, 0.180 mmol) was hydrolyzed by lithium hydroxide 38 mg, 0.904 mmol) in THF/methanol/water (15/7.5/4 ml) to yield 21 mg of the titled compound. 1H NMR (CDCl3, 400 MHz): δ 10.3 (s, 1H), 8.49-8.48 (d, 1H), 8.256-8.252 (d, 1H), 7.85 (s, 1H), 7.81-7.80 (d, 1H), 7.77 (s, 1H), 7.48-7.47 (d, 1H), 7.39-7.37 (dd, 1H), 7.26-6.91 (m, 5H), 5.42 (s, 2H), 3.96 (s, 3H), 3.01 (s, 3H). MS: m/z=510.1 (M+1), HPLC: 96.37% in method B.

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-1ac6885e690548ca8b6e6af08b89460d
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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