Lithium Hydroxide → HCID 90030668, compound

HRID 531527Notes

Reaction equation

HRID 531527 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:46]=[CH:47][CH:48]=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]([N:26]5[CH2:31][CH2:30][N:29]([CH2:32][CH2:33][C:34]#[N:35])[CH2:28][CH2:27]5)[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.CO.O>[F:1][C:2]1[CH:3]=[C:4]([CH:46]=[CH:47][CH:48]=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]([N:26]5[CH2:27][CH2:28][N:29]([CH2:32][CH2:33][C:34]#[N:35])[CH2:30][CH2:31]5)[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 90031138HCID 90031138, compound

Product 1

HCID 90030668HCID 90030668, compoundYield 7.6%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

Using similar reaction conditions as described in step-iii of example-1, 3-(4-(3-(3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperazin-1-yl) propanenitrile (86 mg, 0.13 mmol) was hydrolyzed by lithium hydroxide (27 mg, 6.525 mmol), THF/Methanol/water (15/4/4 ml) to yield 5 mg (5.6% yield) of the titled compound. 1H NMR (CD3OD, 400 MHz): δ 8.481 (s, 1H), 8.407-8.402 (d, 1H), 8.198 (s, 1H), 7.955 (s, 1H), 7.674 (s, 1H), 7.48-7.292 (m, 4H), 7.123-6.98 (m, 4H), 5.439 (s, 2H), 3.8-3.4 (m, 4H), 3.2-3.0 (t, 2H). MS: m/z=506.4 (M+1); HPLC: 98.91% in method A.

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-9a386cf5c76d4a279b6cc520498af882
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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