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

HRID 531602Notes

Reaction equation

HRID 531602 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:44]=[CH:45][CH:46]=1)[CH2:5][CH2:6][N:7]1[CH:11]=[C:10]([C:12]2[C:20]3[C:15](=[N:16][CH:17]=[C:18]([C:21]4[CH:22]=[CH:23][C:24]([O:32][CH3:33])=[C:25]([NH:27][S:28]([CH3:31])(=[O:30])=[O:29])[CH:26]=4)[CH:19]=3)[N:14](S(C3C=CC(C)=CC=3)(=O)=O)[CH:13]=2)[CH:9]=[N:8]1.[OH-].[Li+]>C1COCC1.CO.O>[F:1][C:2]1[CH:3]=[C:4]([CH:44]=[CH:45][CH:46]=1)[CH2:5][CH2:6][N:7]1[CH:11]=[C:10]([C:12]2[C:20]3[C:15](=[N:16][CH:17]=[C:18]([C:21]4[CH:22]=[CH:23][C:24]([O:32][CH3:33])=[C:25]([NH:27][S:28]([CH3:31])(=[O:29])=[O:30])[CH:26]=4)[CH:19]=3)[NH:14][CH:13]=2)[CH:9]=[N:8]1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 118523954N-(5-(3-(1-(3-fluorophenethyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-methoxyphenyl)methane sulfonamide

Product 1

HCID 90031231N-(5-(3-(1-(3-fluorophenethyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-methoxyphenyl)methanesulfonamideYield 40%

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-fluorophenethyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-methoxyphenyl)methane sulfonamide (27 mg, 0.0409 mmol) was hydrolyzed by lithium hydroxide (34 mg, 0.818 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), 9.04 (s, 1H), 8.43-8.42 (d, 1H), 8.176-8.170 (d, 1H), 8.13 (s, 1H), 7.87 (s, 1H), 7.69-7.68 (d, 1H), 7.58-7.57 (m, 2H), 7.32-7.19 (m, 2H), 7.06-7.01 (m, 2H), 4.33-4.38 (t, 2H), 3.89 (s, 3H), 3.21-3.16 (t, 2H), 3.00 (s, 3H). MS: m/z=506.1 (M+1), HPLC: 91.31% in method B.

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-07a0393526a04c05a162b9b913c650ea
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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