Lithium Hydroxide → tert-butyl 4-(4-(3-(1-(3-fluorobenzyl)-5-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperazine-1-carboxylate

HRID 531547Notes

Reaction equation

HRID 531547 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:50]=[CH:51][CH:52]=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]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[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)[CH:8]=[N:7]1.[OH-].[Li+]>C1COCC1.CO.O>[F:1][C:2]1[CH:3]=[C:4]([CH:50]=[CH:51][CH:52]=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]([C:33]([O:35][C:36]([CH3:37])([CH3:38])[CH3:39])=[O:34])[CH2:29][CH2:28]5)=[CH:25][CH:26]=4)[CH:19]=3)[NH:14][CH:13]=2)[CH:8]=[N:7]1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 90030894tert-butyl 4-(4-(3-(1-(3-fluorobenzyl)-5-methyl-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperazine-1-carboxylate

Product 1

HCID 118523906tert-butyl 4-(4-(3-(1-(3-fluorobenzyl)-5-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperazine-1-carboxylateYield 52%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

Using similar reaction conditions as described in step-iii of example-1, tert-butyl 4-(4-(3-(1-(3-fluorobenzyl)-5-methyl-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperazine-1-carboxylate (250 mg, 0.346 mmol) was hydrolyzed by lithium hydroxide (72.8 mg, 1.734 mmol), THF/Methanol/water (2/3/1 ml) to yield 100 mg (52% yield) of the titled compound. 1H NMR (CDCl3, 400 MHz): δ 9.28 (S, 1H), 8.54 (s, 1H), 8.01 (s, 1H), 7.59-7.52 (m, 3H), 7.34-7.27 (m, 2H), 7.05-6.94 (m, 4H), 5.32 (s, 2H), 3.61-3.60 (m, 4H), 3.19 (s, 4H), 2.40 (s, 3H), 1.49 (s, 9H). MS: m/z=657.2 (M+1).

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-914271866deb4ee6aae01aa0d7a0c119
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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