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

HRID 531501Notes

Reaction equation

HRID 531501 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:45]=[CH:46][CH:47]=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]([O:32][CH3:33])=[C:25]([S:27]([NH:30][CH3:31])(=[O:29])=[O:28])[CH:26]=4)[CH:19]=3)[N:14](S(C3C=CC(C)=CC=3)(=O)=O)[CH:13]=2)[C:8]([CH3:44])=[N:7]1.[OH-].[Li+]>C1COCC1.CO.O>[F:1][C:2]1[CH:3]=[C:4]([CH:45]=[CH:46][CH:47]=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]([O:32][CH3:33])=[C:25]([S:27]([NH:30][CH3:31])(=[O:28])=[O:29])[CH:26]=4)[CH:19]=3)[NH:14][CH:13]=2)[C:8]([CH3:44])=[N:7]1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 1185240375-(3-(1-(3-fluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-methoxy-N-methylbenzenesulfonamide

Product 1

HCID 729449545-(3-(1-(3-fluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-methoxy-N-methylbenzenesulfonamideYield 36.06%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

Using similar reaction conditions as described in step-iii of example-1, 5-(3-(1-(3-fluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-methoxy-N-methylbenzenesulfonamide (80 mg, 0.118 mmol) was hydrolyzed by lithium hydroxide (143 mg, 0.593 mmol), THF/Methanol/water (1/1/0.5 mL) to afford 22 mg (36.06% yield) of the titled compound. 1H NMR (CD3OD, 400 MHz): δ 8.47-8.46 (d, 1H), 8.029-8.024 (d, 1H), 7.89-7.86 (m, 2H), 7.41 (s, 1H), 7.38-7.30 (m, 2H), 7.05-6.96 (m, 2H), 6.90-6.85 (m, 1H), 5.36 (s, 2H), 4.00 (s, 3H), 2.53 (s, 3H), 2.21 (s, 3H), 2.18 (s, 3H). MS: m/z=520.1 (M+1), HPLC Purity: 93.81% (Method B).

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-771db35399b9435492572578e0dc6680
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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