Lithium Hydroxide → HCID 72943877, compound

HRID 531549Notes

Reaction equation

HRID 531549 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:44]=[CH:45][CH:46]=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:26]=[CH:25][C:24]([N:27]5[CH2:32][CH2:31][O:30][CH2:29][CH2:28]5)=[CH:23][CH:22]=4)[CH:19]=3)[N:14](S(C3C=CC(C)=CC=3)(=O)=O)[CH:13]=2)[C:8]([CH3:43])=[N:7]1.[OH-].[Li+]>C1COCC1.CO.O>[F:1][C:2]1[CH:3]=[C:4]([CH:44]=[CH:45][CH:46]=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:27]5[CH2:28][CH2:29][O:30][CH2:31][CH2:32]5)=[CH:25][CH:26]=4)[CH:19]=3)[NH:14][CH:13]=2)[C:8]([CH3:43])=[N:7]1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 118524077HCID 118524077, compound

Product 1

HCID 72943877HCID 72943877, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

Using similar reaction conditions as described in step-iii of example-1, 4-(4-(3-(1-(3-fluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl) morpholine (100 mg, 0.157 mmol) was hydrolyzed by lithium hydroxide (33 mg, 0.786 mmol), THF/Methanol/water (5/5/3 ml) to afford 24 mg (32% yield) of the titled compound. 1H NMR (CDCl3, 300 MHz): δ 9.36 (s, 1H), 8.56 (s, 1H), 7.87 (s, 1H), 7.75-7.52 (d, 2H), 7.40-7.30 (m, 1H), 7.10-6.95 (m, 3H), 6.90-6.80 (d, 1H), 5.32 (s, 2H), 3.91-3.88 (m, 4H), 3.23-3.20 (m, 4H), 2.26 (s, 3H), 2.15 (s, 3H). MS: m/z=482.3 (M+1), HPLC Purity: 99.13% Method: B.

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-9c6065f32f544b54860d9ae011daf149
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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