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

HRID 531477Notes

Reaction equation

HRID 531477 reaction equation
[F:1][C:2]1[CH:43]=[CH:42][C:5]([CH2:6][N:7]2[CH:11]=[C:10]([C:12]3[C:20]4[C:15](=[N:16][CH:17]=[C:18]([C:21]5[CH:22]=[C:23]([NH:27][S:28]([CH3:31])(=[O:30])=[O:29])[CH:24]=[CH:25][CH:26]=5)[CH:19]=4)[N:14](S(C4C=CC(C)=CC=4)(=O)=O)[CH:13]=3)[CH:9]=[N:8]2)=[CH:4][CH:3]=1.[OH-].[Li+]>C1COCC1.O.CO>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[CH:11]=[C:10]([C:12]3[C:20]4[C:15](=[N:16][CH:17]=[C:18]([C:21]5[CH:22]=[C:23]([NH:27][S:28]([CH3:31])(=[O:30])=[O:29])[CH:24]=[CH:25][CH:26]=5)[CH:19]=4)[NH:14][CH:13]=3)[CH:9]=[N:8]2)=[CH:42][CH:43]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 90030944N-(3-(3-(1-(4-fluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl) methanesulfonamide

Product 1

HCID 90030543N-(3-(3-(1-(4-fluorobenzyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl) methane sulfonamideYield 1%

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-(4-fluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)methane sulfonamide (137 mg, 0.222 mmol) was hydrolyzed with lithium hydroxide (47 mg, 1.111 mmol) in THF/water/methanol (12/6/3 ml) mixture to afford 1 mg (1% yield) of the title compound. 1H NMR (CD3OD, 600 MHz): δ 8.48 (br, 1H), 8.365-8.361 (d, 1H), 8.183 (s, 1H), 7.922 (s, 1H), 7.64 (s, 1H), 7.568 (m, 1H), 7.52-7.50 (m, 2H), 7.48-7.44 (m, 1H), 7.37-7.34 (m, 2H), 7.31-7.29 (m, 1H), 7.127-7.083 (m, 2H), 5.411 (s, 2H), 3.025 (s, 3H). MS: m/z=462.4 (M+1), HPLC: 90.99% in method B.

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-9fde5ba77af34836aa62082065830d7a
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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