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

HRID 531573Notes

Reaction equation

HRID 531573 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:49]=[CH:50][CH:51]=1)[CH2:5][N:6]1[C:10]([CH3:11])=[C:9]([C:12]2[C:20]3[C:15](=[N:16][CH:17]=[C:18]([C:21]4[CH:22]=[CH:23][C:24]([N:32]5[CH2:37][CH2:36][O:35][CH2:34][CH2:33]5)=[C:25]([NH:27][S:28]([CH3:31])(=[O:30])=[O:29])[CH:26]=4)[CH:19]=3)[N:14](S(C3C=CC(C)=CC=3)(=O)=O)[CH:13]=2)[C:8]([CH3:48])=[N:7]1.[OH-].[Li+]>C1COCC1.CO.O>[F:1][C:2]1[CH:3]=[C:4]([CH:49]=[CH:50][CH:51]=1)[CH2:5][N:6]1[C:10]([CH3:11])=[C:9]([C:12]2[C:20]3[C:15](=[N:16][CH:17]=[C:18]([C:21]4[CH:22]=[CH:23][C:24]([N:32]5[CH2:33][CH2:34][O:35][CH2:36][CH2:37]5)=[C:25]([NH:27][S:28]([CH3:31])(=[O:29])=[O:30])[CH:26]=4)[CH:19]=3)[NH:14][CH:13]=2)[C:8]([CH3:48])=[N:7]1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 118524056N-(5-(3-(1-(3-fluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-morpholino phenyl)methanesulfonamide

Product 1

HCID 72943988N-(5-(3-(1-(3-fluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-morpholinophenyl)methanesulfonamideYield 19.5%

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)-3,5-dimethyl-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-morpholino phenyl)methanesulfonamide (150 mg, 0.205 mmol) was hydrolyzed with lithium hydroxide (43.2 mg, 1.02 mmol) in THF/Methanol/water (2/3/1 ml). This yielded 23 mg (19.49% yield) of pure compound. 1H NMR (CDCl3, 300 MHz): δ 9.17 (s, 1H), 8.55 (s, 1H), 7.86 (s, 2H), 7.75 (s, 1H), 7.32 (s, 3H), 6.99-6.97 (m, 2H), 6.90-6.80 (d, 1H), 5.31 (s, 2H), 3.91-3.88 (m, 4H), 3.10 (s, 3H), 2.92-2.89 (m, 4H), 2.26 (s, 3H), 2.17 (s, 3H). MS: m/z=575.1 (M+1), HPLC Purity: 98.92% Method: B.

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-5eb9f9488a664203ac3908885eb4023c
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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