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

HRID 531608Notes

Reaction equation

HRID 531608 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]3[C:16]([C:17]4[CH:18]=[N:19][N:20]([CH2:22][CH2:23][C:24]5[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=5)[CH:21]=4)=[CH:15][N:14](S(C4C=CC(C)=CC=4)(=O)=O)[C:11]3=[N:12][CH:13]=2)=[CH:4][C:3]=1[NH:40][S:41]([CH3:44])(=[O:43])=[O:42].[OH-].[Li+]>C1COCC1.CO.O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]3[C:16]([C:17]4[CH:18]=[N:19][N:20]([CH2:22][CH2:23][C:24]5[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=5)[CH:21]=4)=[CH:15][NH:14][C:11]3=[N:12][CH:13]=2)=[CH:4][C:3]=1[NH:40][S:41]([CH3:44])(=[O:42])=[O:43]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 118523937N-(2-fluoro-5-(3-(1-phenethyl-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)methanesulfonamide

Product 1

HCID 72944218N-(2-fluoro-5-(3-(1-phenethyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl) methanesulfonamideYield 37.6%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

Using similar reaction conditions as described in step-iii of example-1, N-(2-fluoro-5-(3-(1-phenethyl-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)methanesulfonamide (145 mg, 0.230 mmol) was hydrolyzed by lithium hydroxide (48 mg, 1.15 mmol) in THF/methanol/water (15/5/5 ml) to yield 41 mg (37.6% yield) of the titled compound after purification by preparative TLC(Silicagel-1000 micron) using 50% ethyl acetate in hexane as eluent. 1H NMR (CD3OD, 300 MHz): δ 8.44-8.40 (d, 1H), 8.108-8.101 (d, 1H), 7.83-7.74 (m, 2H), 7.58-7.50 (m, 2H), 7.40-7.10 (m, 5H), 4.46-4.42 (t, 2H), 3.20-3.16 (t, 2H), 3.06 (s, 3H). MS: m/z=476.5 (M+1), HPLC: 93.52% in method A.

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-c8a3980e1a5e4f6fb66a1e051cf74a8d
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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