Lithium Hydroxide → HCID 72943512, compound

HRID 531529Notes

Reaction equation

HRID 531529 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:45]=[CH:46][CH:47]=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:25]=[CH:24][CH:23]=[C:22]([N:26]5[CH2:31][CH2:30][N:29]([CH:32]([CH3:34])[CH3:33])[CH2:28][CH2:27]5)[CH:21]=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:45]=[CH:46][CH:47]=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:25]=[CH:24][CH:23]=[C:22]([N:26]5[CH2:31][CH2:30][N:29]([CH:32]([CH3:34])[CH3:33])[CH2:28][CH2:27]5)[CH:21]=4)[CH:18]=3)[NH:13][CH:12]=2)[CH:8]=[N:7]1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 131735667HCID 131735667, compound

Product 1

HCID 72943512HCID 72943512, compoundYield 13.4%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

Using similar reaction conditions as described in step-iii of example-1, 3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-5-(3-(4-isopropylpiperazin-1-yl)phenyl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine (79 mg, 0.121 mmol) was hydrolyzed by lithium hydroxide (55 mg, 1.21 mmol), THF/Methanol/water (15/5/5 ml) to yield 8 mg (13.3% yield) of the titled compound. 1H NMR (CDCl3, 300 MHz): δ 9.0 (b, 1H), 8.55 (s, 1H), 8.15 (s, 1H), 7.88 (s, 1H), 7.7 (s, 1H), 7.46-7.3 (m, 3H), 7.2-6.9 (m, 3H), 5.389 (s, 2H), 3.4 (m, 4H), 2.7 (m, 4H), 1.4-1.0 (m, 7H). MS: m/z=495.4 (M+1); HPLC: 89.22% in method B.

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-3c21c1c550af46bda54e95e4d158ffff
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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