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

HRID 531612Notes

Reaction equation

HRID 531612 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:42]=[C:43]([F:45])[CH:44]=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:21]=[CH:22][C:23]([F:31])=[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)[CH:8]=[N:7]1.[OH-].[Li+]>C1COCC1.CO.O>[F:45][C:43]1[CH:42]=[C:4]([CH:3]=[C:2]([F:1])[CH:44]=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:21]=[CH:22][C:23]([F:31])=[C:24]([NH:26][S:27]([CH3:30])(=[O:28])=[O:29])[CH:25]=4)[CH:18]=3)[NH:13][CH:12]=2)[CH:8]=[N:7]1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 90031242N-(5-(3-(1-(3,5-difluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-fluorophenyl)methane sulfonamide

Product 1

HCID 72707001N-(5-(3-(1-(3,5-difluorobenzyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-fluoro phenyl)methanesulfonamideYield 85%

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-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-fluorophenyl)methane sulfonamide (53 mg, 0.184 mmol) was hydrolyzed by lithium hydroxide (18 mg, 0.407 mmol) in THF/methanol/water (15/5/5 ml) to yield 34 mg (85% yield) of the titled compound. 1H NMR (CD3OD, 400 MHz): δ 8.44-8.43 (d, 1H), 8.35-8.34 (d, 1H), 8.23 (s, 1H), 7.953-7.951 (d, 1H), 7.80-7.77 (dd, 1H), 7.66 (s, 1H), 7.59-7.55 (m, 1H), 7.34-7.29 (m, 1H), 6.90-6.86 (m, 2H), 5.43 (s, 2H), 305 (s, 3H). MS: m/z=498.1 (M+1), HPLC: 93.19% in method B.

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-33b82d876e094cf7991313873c3e015d
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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