Lithium Hydroxide → HCID 72943881, compound

HRID 531570Notes

Reaction equation

HRID 531570 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:49]=[CH:50][CH:51]=1)[CH2:5][N:6]1[C:10]([CH3:11])=[C:9]([C:12]2[C:20]3[C:15](=[N:16][CH:17]=[C:18]([C:21]4[CH:26]=[CH:25][C:24]([N:27]5[CH2:32][CH2:31][N:30]([CH2:33][CH2:34][N:35]([CH3:37])[CH3:36])[CH2:29][CH2:28]5)=[CH:23][CH:22]=4)[CH:19]=3)[N:14](S(C3C=CC(C)=CC=3)(=O)=O)[CH:13]=2)[C:8]([CH3:48])=[N:7]1.[OH-].[Li+]>C1COCC1.CO.O>[F:1][C:2]1[CH:3]=[C:4]([CH:49]=[CH:50][CH:51]=1)[CH2:5][N:6]1[C:10]([CH3:11])=[C:9]([C:12]2[C:20]3[C:15](=[N:16][CH:17]=[C:18]([C:21]4[CH:22]=[CH:23][C:24]([N:27]5[CH2:32][CH2:31][N:30]([CH2:33][CH2:34][N:35]([CH3:37])[CH3:36])[CH2:29][CH2:28]5)=[CH:25][CH:26]=4)[CH:19]=3)[NH:14][CH:13]=2)[C:8]([CH3:48])=[N:7]1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 90031368HCID 90031368, compound

Product 1

HCID 72943881HCID 72943881, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

Using similar reaction conditions as described in step-iii of intermediate 1, 2-(4-(4-(3-(1-(3-fluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl) piperazin-1-yl)-N,N-dimethylethanamine (190 mg, 0.269 mmol) was hydrolyzed by lithium hydroxide (113 mg, 2.69 mmol), THF/Methanol/water (12/6/3 ml) to afford 34 mg (23% yield) of the titled compound. 1H NMR (CD3OD, 300 MHz): δ 8.432-8.426 (d, 1H), 7.835-7.829 (d, 1H), 7.512-7.475 (m, 2H), 7.367-7.324 (m, 1H), 7.069-6.968 (m, 3H), 6.878-6.845 (m, 1H), 5.349 (s, 2H), 3.68-3.48 (m, 2H), 3.162-3.12 (t, 2H), 2.967 (t, 1H), 2.82-2.715 (m, 8H), 2.206-2.166 (d, 6H), 1.923 (s, 1H). MS: m/z=552.2 (M+1); HPLC: 94.87% in method B.

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-1fd764d9e1c84f3b9c989f48676e9324
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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