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

HRID 531511Notes

Reaction equation

HRID 531511 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:47]=[CH:48][CH:49]=1)[CH2:5][N:6]1[C:10]([CH3:11])=[C:9]([C:12]2[C:20]3[C:15](=[N:16][CH:17]=[C:18]([C:21]4[CH:22]=[CH:23][C:24]([O:32][CH2:33][CH2:34][OH:35])=[C:25]([NH:27][S:28]([CH3:31])(=[O:30])=[O:29])[CH:26]=4)[CH:19]=3)[N:14](S(C3C=CC(C)=CC=3)(=O)=O)[CH:13]=2)[C:8]([CH3:46])=[N:7]1.[OH-].[Li+]>C1COCC1.CO.O>[F:1][C:2]1[CH:3]=[C:4]([CH:47]=[CH:48][CH:49]=1)[CH2:5][N:6]1[C:10]([CH3:11])=[C:9]([C:12]2[C:20]3[C:15](=[N:16][CH:17]=[C:18]([C:21]4[CH:22]=[CH:23][C:24]([O:32][CH2:33][CH2:34][OH:35])=[C:25]([NH:27][S:28]([CH3:31])(=[O:30])=[O:29])[CH:26]=4)[CH:19]=3)[NH:14][CH:13]=2)[C:8]([CH3:46])=[N:7]1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 90031828N-(5-(3-(1-(3-fluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-(2-hydroxyethoxyl)phenyl)methanesulfonamide

Product 1

HCID 72943272N-(5-(3-(1-(3-fluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-(2-hydroxyethoxy)phenyl)methanesulfonamideYield 15.38%

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)-3,5-dimethyl-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-(2-hydroxyethoxyl)phenyl) methanesulfonamide (150 mg, 0.208 mmol) was hydrolyzed by lithium hydroxide (88 mg, 2.08 mmol), THF/Methanol/water (3/3/1.5 ml) to afford 15 mg (15.38% yield) of the title compound. 1H NMR (DMSO-d6, 300 MHz): δ11.9 (s, 1H), 9.00 (s, 1H), 8.49 (s, 1H), 7.81 (s, 1H), 7.59 (s, 1H), 7.51-7.41 (m, 3H), 7.15-7.12 (d, 1H), 7.05-7.03 (m, 1H), 6.87 (s, 1H), 4.06 (m, 2H), 3.78 (m, 2H), 3.00 (s, 3H), 2.18-2.14 (d, 6H), MS: m/z=550.1 (M+1), HPLC: 87.11% in Method B.

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-0add5280cbe3461b82b52b40f7c167a9
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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