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

HRID 531516Notes

Reaction equation

HRID 531516 reaction equation
[CH3:1][N:2]([CH3:52])[CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:14]=[C:15]3[C:21]([C:22]4[C:23]([CH3:36])=[N:24][N:25]([CH2:28][C:29]5[CH:34]=[CH:33][CH:32]=[C:31]([F:35])[CH:30]=5)[C:26]=4[CH3:27])=[CH:20][N:19](S(C4C=CC(C)=CC=4)(=O)=O)[C:16]3=[N:17][CH:18]=2)=[CH:9][C:8]=1[NH:47][S:48]([CH3:51])(=[O:50])=[O:49].[OH-].[Li+]>C1COCC1.CO.O>[CH3:52][N:2]([CH3:1])[CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:14]=[C:15]3[C:21]([C:22]4[C:23]([CH3:36])=[N:24][N:25]([CH2:28][C:29]5[CH:34]=[CH:33][CH:32]=[C:31]([F:35])[CH:30]=5)[C:26]=4[CH3:27])=[CH:20][NH:19][C:16]3=[N:17][CH:18]=2)=[CH:9][C:8]=1[NH:47][S:48]([CH3:51])(=[O:50])=[O:49]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 90030630N-(2-(3-(dimethylamino)propoxy)-5-(3-(1-(3-fluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)methanesulfonamide

Product 1

HCID 72943274N-(2-(3-(dimethylamino)propoxy)-5-(3-(1-(3-fluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)methanesulfonamideYield 16.9%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

Using similar reaction conditions as described in step-iii of example-1, N-(2-(3-(dimethylamino)propoxy)-5-(3-(1-(3-fluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)methanesulfonamide (40 mg, 0.05 mmol) was hydrolyzed by lithium hydroxide (4 mg, 0.16 mmol), THF/methanol/water (1/1/0.5 ml) to afford 5 mg (16% yield) of the titled compound after purification by preparative TLC (SiO2)-eluted by 5% methanol in DCM. 1H NMR (CDCl3, 400 MHz): δ 8.88 (s, 1H), 8.54-8.53 (d, 1H), 7.84 (s, 1H), 7.808-7.803 (d, 1H), 7.33-7.23 (m, 3H), 7.05-7.03 (d, 1H), 6.99-6.90 (m, 2H), 6.87-6.852 (d, 1H), 5.31 (s, 2H), 4.16-4.13 (t, 2H), 2.96 (s, 3H), 2.52-2.49 (t, 2H), 2.31 (s, 6H), 2.25 (s, 3H), 2.17 (s, 3H), 2.00-1.97 (m, 2H). MS: m/z=591.4 (M+1), HPLC: 91.28% in method B.

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-2c69c47746684bf0b445eff76ae6a240
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

Loading…