Lithium Hydroxide → HCID 72943270, compound

HRID 531507Notes

Reaction equation

HRID 531507 reaction equation
[F:1][C:2]1[CH:47]=[CH:46][C:45]([F:48])=[CH:44][C:3]=1[CH2:4][N:5]1[C:9]([CH3:10])=[C:8]([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)[C:7]([CH3:43])=[N:6]1.[OH-].[Li+]>C1COCC1.CO.O>[F:1][C:2]1[CH:47]=[CH:46][C:45]([F:48])=[CH:44][C:3]=1[CH2:4][N:5]1[C:9]([CH3:10])=[C:8]([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:28])=[O:29])[CH:25]=4)[CH:18]=3)[NH:13][CH:12]=2)[C:7]([CH3:43])=[N:6]1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 90031121HCID 90031121, compound

Product 1

HCID 72943270HCID 72943270, compoundYield 28.2%

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-(2,5-difluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-methoxy phenyl)methanesulfonamide (100 mg, 0.14 mmol) was hydrolyzed by lithium hydroxide (30.3 mg, 0.722 mmol), THF/Methanol/water (3/3/1 ml) to afford 13 mg (28.2% yield) of the titled compound after purification by column (SiO2-eluted by 2% MeOH in CHCl3). 1H NMR (CDCl3, 300 MHz): δ 9.37 (s, 1H), 8.54 (s, 1H), 7.84-7.78 (m, 2H), 7.37-7.35 (m, 1H), 7.02-6.99 (m, 1H), 6.95-6.85 (m, 1H), 6.80-6.60 (m, 2H), 5.29 (s, 2H), 3.94 (s, 3H), 2.99 (s, 3H), 2.25 (s, 3H), 2.17 (s, 3H). MS: m/z=538.1 (M+1), HPLC Purity: 91.44%, (Method: B).

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-886932326b7a4634a71f51f8f5e9c559
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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