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

HRID 531484Notes

Reaction equation

HRID 531484 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:41]=[CH:42][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:1][C:2]1[CH:3]=[C:4]([CH:41]=[CH:42][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 90031282N-(3-(3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl) methanesulfonamide

Product 1

HCID 72944851N-(3-(3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl) methanesulfonamideYield 12.7%

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-fluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)methane sulfonamide (106 mg, 0.17 mmol) was hydrolyzed with lithium hydroxide (36 mg, 0.861 mmol) in THF/water/methanol (12/6/2 ml) mixture to afford 10 mg (12.6% yield) of the pure product. 1H NMR (CD3OD, 300 MHz): δ 8.464-8.458 (d, 1H), 8.352-8.347 (d, 1H), 8.185 (s, 1H), 7.923 (s, 1H), 7.64 (s, 1H), 7.544-7.538 (m, 1H), 7.514-7.431 (m, 2H), 7.37-7.26 (m, 2H), 7.115-6.997 (m, 2H), 5.426 (s, 2H), 3.002 (s, 3H). MS: m/z=461.8 (M+1), HPLC: 96.947% in method A.

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-796c0b602ce446cf8b916d31b57e06e7
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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