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

HRID 531497Notes

Reaction equation

HRID 531497 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:45]=[CH:46][CH:47]=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]([O:33][CH3:34])=[C:24]([NH:26][S:27]([CH:30]5[CH2:32][CH2:31]5)(=[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:1][C:2]1[CH:3]=[C:4]([CH:45]=[CH:46][CH:47]=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]([O:33][CH3:34])=[C:24]([NH:26][S:27]([CH:30]5[CH2:31][CH2:32]5)(=[O:29])=[O:28])[CH:25]=4)[CH:18]=3)[NH:13][CH:12]=2)[CH:8]=[N:7]1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 90031081N-(5-(3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-methoxyphenyl)cyclo propanesulfonamide

Product 1

HCID 72944952N-(5-(3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-methoxy phenyl)cyclopropanesulfonamideYield 8.19%

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-fluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-methoxyphenyl)cyclo propanesulfonamide (80 mg, 0.119 mmol) was hydrolyzed by lithium hydroxide (0.0109 g, 0.238 mmol), THF/Methanol/water (12/8/4 mL) to afford 5 mg (8.19% yield) of the titled compound. 1H NMR (DMSO-d6, 300 MHz): δ 11.8 (s, 1H), 9.04 (s, 1H), 8.44-8.42 (d, 2H), 8.29 (s, 1H), 7.96 (s, 1H), 7.77 (s, 1H), 7.61-7.58 (m, 2H0, 7.20-7.10 (m, 4H), 5.41 (s, 2H), 3.88 (s, 3H), 0.92-0.88 (m, 4H). MS: m/z=517.8 (M+1), HPLC: 84.12% Method B.

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-e81d881e5e3e4b03911c5e9ea084b8bb
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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