Lithium Hydroxide → HCID 72944854, compound

HRID 531489Notes

Reaction equation

HRID 531489 reaction equation
[CH2:1]([N:8]1[CH:12]=[C:11]([C:13]2[C:21]3[C:16](=[N:17][CH:18]=[C:19]([C:22]4[CH:23]=[C:24]([NH:28][S:29]([CH3:32])(=[O:31])=[O:30])[CH:25]=[CH:26][CH:27]=4)[CH:20]=3)[N:15](S(C3C=CC(C)=CC=3)(=O)=O)[CH:14]=2)[CH:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Li+]>CO.O.C1COCC1>[CH2:1]([N:8]1[CH:12]=[C:11]([C:13]2[C:21]3[C:16](=[N:17][CH:18]=[C:19]([C:22]4[CH:23]=[C:24]([NH:28][S:29]([CH3:32])(=[O:31])=[O:30])[CH:25]=[CH:26][CH:27]=4)[CH:20]=3)[NH:15][CH:14]=2)[CH:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 90030421HCID 90030421, compound

Product 1

HCID 72944854HCID 72944854, compoundYield 9%

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-benzyl-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)methanesulfonamide (60 mg, 0.1 mmol) was hydrolyzed by lithium hydroxide (9 mg, 0.2 mmol) in methanol/water/THF (1/1/1 ml) which afforded 4 mg (9% yield) after purification by preparative TLC (silicagel-1000 micron) using 5% methanol in chloroform as eluent. 1H NMR (DMSO-d6, 300 MHz): δ 8.46-8.45 (d, 1H), 8.34-8.33 (d, 1H), 8.14 (s, 1H), 7.9 (s, 1H), 7.62 (s, 1H), 7.54 (m, 1H), 7.5-7.43 (m, 2H), 7.37-7.33 (m, 2H), 7.3-7.27 (m, 3H), 5.4 (s, 2H), 3.0 (s, 3H). MS: m/z=443.6 (M+1), HPLC: 88.2%, Method A.

Workup

  1. customreaction conditions
  2. customafforded 4 mg (9% yield)
  3. customafter purification by preparative TLC (silicagel-1000 micron)

Sources & evidence

ORD record
ord-7868189da3f64be18b7ee01aebe57a85
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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