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

HRID 531605Notes

Reaction equation

HRID 531605 reaction equation
[F:1][C:2]1[CH:46]=[CH:45][C:5]([CH2:6][CH2:7][N:8]2[CH:12]=[C:11]([C:13]3[C:21]4[C:16](=[N:17][CH:18]=[C:19]([C:22]5[CH:23]=[CH:24][C:25]([O:33][CH3:34])=[C:26]([NH:28][S:29]([CH3:32])(=[O:31])=[O:30])[CH:27]=5)[CH:20]=4)[N:15](S(C4C=CC(C)=CC=4)(=O)=O)[CH:14]=3)[CH:10]=[N:9]2)=[CH:4][CH:3]=1.[OH-].[Li+]>C1COCC1.CO.O>[F:1][C:2]1[CH:46]=[CH:45][C:5]([CH2:6][CH2:7][N:8]2[CH:12]=[C:11]([C:13]3[C:21]4[C:16](=[N:17][CH:18]=[C:19]([C:22]5[CH:23]=[CH:24][C:25]([O:33][CH3:34])=[C:26]([NH:28][S:29]([CH3:32])(=[O:30])=[O:31])[CH:27]=5)[CH:20]=4)[NH:15][CH:14]=3)[CH:10]=[N:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 118523952N-(5-(3-(1-(4-fluorophenethyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-methoxyphenyl) methanesulfonamide

Product 1

HCID 72944217N-(5-(3-(1-(4-fluorophenethyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-methoxyphenyl)methanesulfonamideYield 41.8%

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-(4-fluorophenethyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-methoxyphenyl) methanesulfonamide (25 mg, 0.0379 mmol) was hydrolyzed by lithium hydroxide (15 mg, 0.379 mmol) in THF/methanol/water (2/2/1 ml) to yield 8 mg (40.0% yield) of the titled compound. 1H NMR (DMSO-d6, 300 MHz): δ 11.7 (s, 1H), 9.034-9.035 (d, 1H), 8.43-8.42 (d, 1H), 8.20 (s, 1H), 8.14 (s, 1H), 7.87 (s, 1H), 7.69-7.68 (d, 2H), 7.58-7.56 (m, 2H), 7.26-7.18 (m, 3H), 7.11-7.05 (m, 2H), 4.39-4.35 (t, 2H), 3.89 (s, 3H), 3.18-3.13 (t, 2H), 3.00 (s, 3H). MS: m/z=506.5 (M+1), HPLC: 96.65% in method B.

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-da9165bec6d04976ac39831e1f71d1b8
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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