Lithium Hydroxide → HCID 72944852, compound

HRID 531485Notes

Reaction equation

HRID 531485 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:41]=[CH:42][CH:43]=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]=[C:22]([NH:26][S:27]([CH3:30])(=[O:29])=[O:28])[CH:23]=[CH:24][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.O.CO>[Cl:1][C:2]1[CH:3]=[C:4]([CH:41]=[CH:42][CH:43]=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]=[C:22]([NH:26][S:27]([CH3:30])(=[O:28])=[O:29])[CH:23]=[CH:24][CH:25]=4)[CH:18]=3)[NH:13][CH:12]=2)[CH:8]=[N:7]1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 90031867HCID 90031867, compound

Product 1

HCID 72944852HCID 72944852, compoundYield 18%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

Using similar reaction conditions as described in step-iii of example-1, N-(3-(3-(1-(3-chlorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)methane sulfonamide (90 mg, 0.14 mmol) was hydrolyzed with lithium hydroxide (18 mg, 0.42 mmol) in THF/water/methanol (1/0.5/1 ml) mixture to afford 12 mg (18% yield) of the pure product after purification by preparative TLC (Silicagel-1000 micron) using 10% ethyl acetate in hexane as eluent. 1H NMR (DMSO-d6, 400 MHz): δ 11.83 (s, 1H), 9.85 (s, 1H), 8.48-8.47 (d, 1H), 8.43 (s, 1H), 8.346-8.342 (d, 1H), 7.90 (s, 1H), 7.80-7.79 (d, 1H), 7.51-7.25 (m, 8H), 5.40 (s, 2H), 3.06 (s, 3H). MS: m/z=478.2 (M+1), HPLC: 92.01% (method B).

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-dc3d909dede5467eae0a24c4c1cef6b1
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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