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

HRID 531479Notes

Reaction equation

HRID 531479 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:41]=[C:42]([F:44])[CH:43]=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]=[C:22]([NH:26][S:27]([CH3:30])(=[O:29])=[O:28])[CH:23]=[CH:24][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.O.CO>[F:44][C:42]1[CH:41]=[C:4]([CH:3]=[C:2]([F:1])[CH:43]=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]=[C:22]([NH:26][S:27]([CH3:30])(=[O:28])=[O:29])[CH:23]=[CH:24][CH:25]=4)[CH:18]=3)[NH:13][CH:12]=2)[CH:8]=[N:7]1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 90030771N-(3-(3-(1-(3,5-difluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)methane sulfonamide

Product 1

HCID 72944750N-(3-(3-(1-(3,5-difluorobenzyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl) methane sulfonamideYield 8.8%

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-(3,5-difluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)methane sulfonamide (300 mg, 0.473 mmol) was hydrolyzed with lithium hydroxide (40 mg, 0.946 mmol) in THF/water/methanol (15/10/5 ml) mixture to afford 20 mg (8.8% yield) of the desired compound. 1H NMR (DMSO-d6, 400 MHz): δ 11.82 (s, 1H), 9.82 (s, 1H), 8.48-8.47 (d, 1H), 8.43 (s, 1H), 8.355-8.350 (d, 1H), 8.00 (s, 1H), 7.71-7.80 (d, 1H), 7.53-7.46 (m, 3H), 7.25-7.23 (m, 2H), 6.98-6.97 (d, 2H), 5.42 (s, 2H), 3.05 (s, 3H). MS: m/z=479.8 (M+1), HPLC: 94.78% (Method-B).

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-cd23dee7cc8a4d489f02c73282a47af3
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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