Lithium Hydroxide → N-(5-(3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-morpholinophenyl)methanesulfonamide

HRID 531499Notes

Reaction equation

HRID 531499 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:47]=[CH:48][CH:49]=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]=[CH:22][C:23]([N:31]5[CH2:36][CH2:35][O:34][CH2:33][CH2:32]5)=[C:24]([NH:26][S:27]([CH3:30])(=[O:29])=[O:28])[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:47]=[CH:48][CH:49]=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]=[CH:22][C:23]([N:31]5[CH2:32][CH2:33][O:34][CH2:35][CH2:36]5)=[C:24]([NH:26][S:27]([CH3:30])(=[O:29])=[O:28])[CH:25]=4)[CH:18]=3)[NH:13][CH:12]=2)[CH:8]=[N:7]1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 118523922N-(5-(3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-morpholinophenyl) methanesulfonamide

Product 1

HCID 72944953N-(5-(3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-morpholinophenyl)methanesulfonamideYield 18.2%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

Using similar reaction conditions as described in step-iii of example-1, N-(5-(3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-morpholinophenyl) methanesulfonamide (240 mg, 0.342 mmol) was hydrolyzed by lithium hydroxide (143 mg, 3.42 mmol), THF/Methanol/water (20/8/8 mL) to yield 34 mg (18%) of the titled compound. 1H NMR (DMSO-D6, 400 MHz): δ 11.8 (s, 1H), 8.618 (s, 1H), 8.469-8.464 (m, 1H), 8.421 (s, 1H), 8.317-8.313 (d, 1H), 7.963 (s, 1H), 7.782-7.777 (d, 1H), 7.649-7.645 (d, 1H), 7.58-7.52 (m, 1H), 7.44-7.366 (m, 2H), 7.16-7.08 (m, 3H), 5.402 (s, 2H), 3.80.3-3.791 (m, 4H), 3.197 (s, 3H), 2.898-2.887 (m, 4H). MS: m/z=546.8 (M+1); HPLC: 96.04% in method B.

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-d6239d6f638b4359b58e877530eb1dd0
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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