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

HRID 531584Notes

Reaction equation

HRID 531584 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:39]=[CH:40][CH:41]=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]([NH2:28])[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:39]=[CH:40][CH:41]=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]([NH2:28])[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 1185240365-(3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-methoxy pyridin-3-amine

Product 1

HCID 900306345-(3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-methoxypyridin-3-amineYield 17.1%

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)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-methoxypyridin-3-amine (80 mg, 0.14 mmol) was hydrolyzed with lithium hydroxide (12 mg, 0.28 mmol) in THF/methanol/water (2/2/1 mL) to yield 10 mg (17.1% yield) after purification by preparative TLC(Silicagel-1000 micron) using 5% methanol in chloroform as eluent. 1H NMR (CD3OD, 300 MHz): δ 8.37 (s, 1H), 8.27 (s, 1H), 8.17 (s, 1H), 7.91 (s, 1H), 7.717-7.712 (d, 1H), 7.61 (s, 1H), 7.36-7.29 (m, 2H), 7.10-6.98 (m, 3H), 5.41 (s, 2H), 4.00 (s, 3H). MS: m/z=415.2 (M+1), HPLC: 88.73% in method B.

Workup

  1. customreaction conditions
  2. customto yield 10 mg (17.1% yield)
  3. customafter purification by preparative TLC(Silicagel-1000 micron)

Sources & evidence

ORD record
ord-a006b84c09a94b058d260ed0853cb320
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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