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

HRID 531588Notes

Reaction equation

HRID 531588 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:43]=[CH:44][CH:45]=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]=[C:22]([NH:28][S:29]([CH3:32])(=[O:31])=[O:30])[C:23]([O:26][CH3:27])=[N:24][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:43]=[CH:44][CH:45]=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]=[C:22]([NH:28][S:29]([CH3:32])(=[O:30])=[O:31])[C:23]([O:26][CH3:27])=[N:24][CH:25]=4)[CH:18]=3)[NH:13][CH:12]=2)[CH:8]=[N:7]1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 118523938N-(5-(3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-methoxypyridin-3-yl) methanesulfonamide

Product 1

HCID 72944101N-(5-(3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-methoxypyridin-3-yl)methanesulfonamideYield 31.8%

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-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-methoxypyridin-3-yl) methanesulfonamide (70 mg, 0.108 mmol) was hydrolyzed with lithium hydroxide (14 mg, 0.324 mmol) in THF/methanol/water (3.5/3.5/0.5 mL) to yield 17 mg (31.8% yield) after purification by preparative TLC (Silicagel-1000 micron) using 5% methanol in chloroform as eluent. 1H NMR (CD3OD, 300 MHz): δ 8.42 (s, 1H), 8.34-8.33 (s, 1H), 8.288-8.280 (d, 1H), 8.22 (s, 1H), 8.04-8.03 (d, 1H), 7.934-7.931 (d, 1H), 8.04-8.03 (d, 1H), 7.934-7.931 (d, 1H), 7.65 (s, 1H), 7.38-7.35 (q, 1H), 7.12-7.09 (d, 1H), 7.03-6.99 (m, 2H), 5.42 (s, 2H), 4.06 (s, 3H), 3.03 (s, 3H). MS: m/z=492.8 (M+1), HPLC: 96.33% in method B.

Workup

  1. customreaction conditions
  2. customto yield 17 mg (31.8% yield)
  3. customafter purification by preparative TLC (Silicagel-1000 micron)

Sources & evidence

ORD record
ord-75dd3324ccf847829fb187e0fd47aeaa
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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