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

HRID 531582Notes

Reaction equation

HRID 531582 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[C:11]3[C:17]([C:18]4[CH:19]=[N:20][N:21]([CH2:23][CH2:24][C:25]5[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=5)[CH:22]=4)=[CH:16][N:15](S(C4C=CC(C)=CC=4)(=O)=O)[C:12]3=[N:13][CH:14]=2)=[CH:5][C:4]=1[NH:41][S:42]([CH3:45])(=[O:44])=[O:43].[OH-].[Li+]>C1COCC1.CO.O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[C:11]3[C:17]([C:18]4[CH:19]=[N:20][N:21]([CH2:23][CH2:24][C:25]5[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=5)[CH:22]=4)=[CH:16][NH:15][C:12]3=[N:13][CH:14]=2)=[CH:5][C:4]=1[NH:41][S:42]([CH3:45])(=[O:44])=[O:43]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 118523955N-(2-methoxy-5-(3-(1-phenethyl-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)methanesulfonamide

Product 1

HCID 72943991N-(2-methoxy-5-(3-(1-phenethyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl) methanesulfonamideYield 17.2%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

Using similar reaction conditions as described in step-iii of example-1, N-(2-methoxy-5-(3-(1-phenethyl-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)methanesulfonamide (100 mg, 0.155 mmol) was hydrolyzed by lithium hydroxide (13 mg, 0.311 mmol) in THF/methanol/water (5/1/2 mL) to afford 13 mg of the titled compound. 1H NMR (DMSO-d6, 400 MHz): δ 9.07 (s, 1H), 8.45-8.44 (d, 1H), 8.186-8.182 (d, 1H), 8.13, s 1H), 7.89 (s, 1H), 7.716-7.710 (d, 1H), 7.60-7.59 (m, 2H), 7.31-7.28 (m, 2H), 7.24-7.19 (m, 4H), 4.43-4.39 (t, 2H), 3.91 (s, 3H), 3.20-3.16 (t, 2H), 3.02 (s, 3H). MS: m/z=487.8 (M+1), HPLC: 95.48% in method A.

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-127f99daf0b043e797c20db812db048b
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

Loading…