Lithium Hydroxide → 2-(4-(4-(3-(1-(3-fluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperazin-1-yl)ethanol

HRID 531541Notes

Reaction equation

HRID 531541 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:47]=[CH:48][CH:49]=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][OH:35])[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]([CH3:46])=[N:7]1.[OH-].[Li+]>C1COCC1.CO.O>[F:1][C:2]1[CH:3]=[C:4]([CH:47]=[CH:48][CH:49]=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][OH:35])[CH2:29][CH2:28]5)=[CH:25][CH:26]=4)[CH:19]=3)[NH:14][CH:13]=2)[C:8]([CH3:46])=[N:7]1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 900313392-(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)ethanol

Product 1

HCID 729436412-(4-(4-(3-(1-(3-fluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperazin-1-yl)ethanolYield 2.2%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

Using similar reaction conditions as described in step-iii of example-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)ethanol (200 mg, 0.259 mmol) was hydrolyzed by lithium hydroxide (108 mg, 2.59 mmol), THF/Methanol/water (5/5/2.5 ml) to yield 3 mg (2.2% yield) of the titled compound. 1H NMR (CD3OD, 300 MHz): δ 8.34 (s, 1H), 7.75-7.74 (d, 1H), 7.44-7.41 (m, 2H), 7.28-7.27 (m, 2H), 7.00-6.7 (m, 4H), 6.52-6.51 (d, 1H), 5.26 (s, 2H), 3.73-3.69 (t, 2H), 3.26 (m, 4H), 2.91 (m, 4H), 2.79-2.77 (t, 2H), 2.12-2.08 (m, 6H). MS: m/z=525.2 (M+1), HPLC: 80.69% in method A.

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-83c504bae0674b97bf5a535afda0af57
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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