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

HRID 531491Notes

Reaction equation

HRID 531491 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:43]=[CH:44][CH:45]=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:31][CH3:32])=[C:24]([NH:26][S:27]([CH3:30])(=[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:43]=[CH:44][CH:45]=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:31][CH3:32])=[C:24]([NH:26][S:27]([CH3:30])(=[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 90030288N-(5-(3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-methoxyphenyl) methane sulfonamide

Product 1

HCID 90030999N-(5-(3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-methoxy phenyl) methanesulfonamideYield 15%

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) methane sulfonamide (150 mg, 0.232 mmol) was hydrolyzed with lithium hydroxide (49 mg, 1.162 mmol) in THF/Methanol/Water (15/6/4 mL) to yield 17 mg (15% yield) after purification by preparative TLC (Silicagel-1000 micron) using 2% methanol in chloroform as eluent. 1H NMR (CD3OD, 400 MHz): δ 8.446-8.441 (d, 1H), 8.327-8.322 (d, 1H), 8.215 (s, 1H), 7.936 (s, 1H), 7.746-7.741 (d, 1H), 7.643 (s, 1H). 7.577-7.551 (m, 1H), 7.398-7.364 (m, 1H), 7.21-7.188 (d, 1H), 7.210-7.188 (d, 1H), 7.137-7.118 (d, 1H), 7.067-7.026 (m, 2H), 5.426 (s, 2H), 3.98 (s, 3H), 3.002 (s, 3H). MS: m/z=491.8 (M+1), HPLC: 97.01% in method A.

Workup

  1. customreaction conditions
  2. customto yield 17 mg (15% yield)
  3. customafter purification by preparative TLC (Silicagel-1000 micron)

Sources & evidence

ORD record
ord-9839258ea829493eae6510e8e28e1819
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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