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

HRID 531543Notes

Reaction equation

HRID 531543 reaction equation
[F:1][C:2]1[CH:53]=[CH:52][C:51]([F:54])=[CH:50][C:3]=1[CH2:4][N:5]1[C:9]([CH3:10])=[C:8]([C:11]2[C:19]3[C:14](=[N:15][CH:16]=[C:17]([C:20]4[CH:25]=[CH:24][C:23]([N:26]5[CH2:31][CH2:30][N:29]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:28][CH2:27]5)=[CH:22][CH:21]=4)[CH:18]=3)[N:13](S(C3C=CC(C)=CC=3)(=O)=O)[CH:12]=2)[C:7]([CH3:49])=[N:6]1.[OH-].[Li+]>C1COCC1.CO.O>[F:1][C:2]1[CH:53]=[CH:52][C:51]([F:54])=[CH:50][C:3]=1[CH2:4][N:5]1[C:9]([CH3:10])=[C:8]([C:11]2[C:19]3[C:14](=[N:15][CH:16]=[C:17]([C:20]4[CH:25]=[CH:24][C:23]([N:26]5[CH2:27][CH2:28][N:29]([C:32]([O:34][C:35]([CH3:37])([CH3:38])[CH3:36])=[O:33])[CH2:30][CH2:31]5)=[CH:22][CH:21]=4)[CH:18]=3)[NH:13][CH:12]=2)[C:7]([CH3:49])=[N:6]1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 90033968tert-butyl 4-(4-(3-(1-(2,5-difluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperazine-1-carboxylate

Product 1

HCID 118523924tert-butyl 4-(4-(3-(1-(2,5-difluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperazine-1-carboxylateYield 25.2%

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-(2,5-difluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperazine-1-carboxylate (230 mg, 0.305 mmol) was hydrolyzed by lithium hydroxide (129 mg, 3.05 mmol), THF/Methanol/water (12/4/4 ml) to afford 46 mg (25.2% yield) of the titled compound. MS: m/z=599.3 (M+1).

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-90a8d94894a44d0cbed8aec0111add78
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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