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

HRID 531610Notes

Reaction equation

HRID 531610 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][C:23]5[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[CH:24]=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][C:23]5[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[CH:24]=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 90033300N-(2-fluoro-5-(3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)methanesulfonamide

Product 1

HCID 72944219N-(2-fluoro-5-(3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)methanesulfonamideYield 48.8%

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-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)methanesulfonamide (60 mg, 0.094 mmol) was hydrolyzed with lithium hydroxide (20 mg, 0.474 mmol) in THF/methanol/water (15/5/5 mL) to yield 22 mg (48.8% yield). 1H NMR (CD3OD, 400 MHz): δ 8.467-8.462 (d, 1H), 8.36-8.35 (d, 1H), 8.22 (s, 1H), 7.95 (s, 1H), 7.84-7.80 (dd, 1H), 7.63-7.57 (m, 1H), 7.44-7.32 (m, 2H), 7.16-7.12 (d, 1H), 7.10-7.02 (m, 2H). MS: m/z=480.3 (M+1), HPLC: 92.50% in method B.

Workup

  1. customreaction conditions
  2. customto yield 22 mg (48.8% yield)

Sources & evidence

ORD record
ord-93996c9ef6da46eb93878317902f73b4
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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