Lithium Hydroxide → HCID 72943513, compound

HRID 531531Notes

Reaction equation

HRID 531531 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:25]=[CH:24][CH:23]=[C:22]([N:26]5[CH2:31][CH2:30][N:29]([CH3:32])[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: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:25]=[CH:24][CH:23]=[C:22]([N:26]5[CH2:31][CH2:30][N:29]([CH3:32])[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 118524066HCID 118524066, compound

Product 1

HCID 72943513HCID 72943513, compoundYield 53.9%

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-methylpiperazin-1-yl)phenyl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine (74 mg, 0.119 mmol) was hydrolyzed by lithium hydroxide (50 mg, 1.19 mmol), THF/Methanol/water (12/6/3 ml) to yield 8 mg (30 mg 53.9% yield) of the titled compound. 1H NMR (CDCl3, 300 MHz): δ 9.4 (b, 1H), 8.566-8.559 (d, 1H), 8.185-8.178 (d, 1H), 7.874 (s, 1H), 7.706 (s, 1H), 7.451-7.443 (d, 1H), 7.413-7.3 (m, 2H), 7.2-6.956 (m, 5H), 5.392 (s, 2H), 3.340-3.307 (m, 4H), 2.669-2.636 (m, 4H), 2.401 (s, 3H). MS: m/z=467.4 (M+1); HPLC: 98.239% in method B.

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-900e2a68af5c4c25821280daf9aa923c
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

Loading…