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

HRID 531487Notes

Reaction equation

HRID 531487 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:42]=[CH:43][CH:44]=1)[CH2:6][N:7]1[CH:11]=[C:10]([C:12]2[C:20]3[C:15](=[N:16][CH:17]=[C:18]([C:21]4[CH:22]=[C:23]([NH:27][S:28]([CH3:31])(=[O:30])=[O:29])[CH:24]=[CH:25][CH:26]=4)[CH:19]=3)[N:14](S(C3C=CC(C)=CC=3)(=O)=O)[CH:13]=2)[CH:9]=[N:8]1)#[N:2].[OH-].[Li+]>C1COCC1.O.CO>[C:1]([C:3]1[CH:4]=[C:5]([CH:42]=[CH:43][CH:44]=1)[CH2:6][N:7]1[CH:11]=[C:10]([C:12]2[C:20]3[C:15](=[N:16][CH:17]=[C:18]([C:21]4[CH:22]=[C:23]([NH:27][S:28]([CH3:31])(=[O:30])=[O:29])[CH:24]=[CH:25][CH:26]=4)[CH:19]=3)[NH:14][CH:13]=2)[CH:9]=[N:8]1)#[N:2]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 90031340N-(3-(3-(1-(3-cyanobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl) methane sulfonamide

Product 1

HCID 72944853N-(3-(3-(1-(3-cyanobenzyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl) methanesulfonamideYield 15.2%

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-cyanobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl) methane sulfonamide (90 mg, 0.14 mmol) was hydrolyzed with lithium hydroxide (18 mg, 0.43 mmol) in THF/water/methanol (1/0.5/1 ml) mixture to afford 10 mg (15% yield) of the pure product after purification by preparative TLC (Silicagel-1000 micron) using 10% ethyl acetate in hexane as eluent. 1H NMR (DMSO-d6, 400 MHz): δ11.88 (s, 1H), 9.85 (b, 1H), 8.478-8.475 (d, 1H), 8.43 (s, 1H), 8.34 (s, 1H), 7.986 (s, 1H), 7.80-7.75 (m, 3H), 7.60-7.45 (m, 5H), 7.26-7.24 (d, 1H) 5.46 (s, 2H), 3.05 (s, 3H) MS: m/z=469.4 (M+1), HPLC 93.92%, (method A).

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-cbc281d73f7e4d86b1930136d60d3387
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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