Lithium Hydroxide → HCID 118523993, compound

HRID 531567Notes

Reaction equation

HRID 531567 reaction equation
[CH:1]1([C:4]2[N:9]=[C:8]3[N:10](S(C4C=CC(C)=CC=4)(=O)=O)[CH:11]=[C:12]([C:13]4[C:14]([CH3:27])=[N:15][N:16]([CH2:19][C:20]5[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[CH:21]=5)[C:17]=4[CH3:18])[C:7]3=[CH:6][C:5]=2[C:38]2[CH:43]=[CH:42][C:41]([N:44]3[CH2:49][CH2:48][N:47]([C:50]([O:52][C:53]([CH3:56])([CH3:55])[CH3:54])=[O:51])[CH2:46][CH2:45]3)=[CH:40][CH:39]=2)[CH2:3][CH2:2]1.[OH-].[Li+]>CO.O>[CH:1]1([C:4]2[N:9]=[C:8]3[NH:10][CH:11]=[C:12]([C:13]4[C:14]([CH3:27])=[N:15][N:16]([CH2:19][C:20]5[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[CH:21]=5)[C:17]=4[CH3:18])[C:7]3=[CH:6][C:5]=2[C:38]2[CH:43]=[CH:42][C:41]([N:44]3[CH2:45][CH2:46][N:47]([C:50]([O:52][C:53]([CH3:56])([CH3:55])[CH3:54])=[O:51])[CH2:48][CH2:49]3)=[CH:40][CH:39]=2)[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 118524039HCID 118524039, compound

Product 1

HCID 118523993HCID 118523993, compoundYield 16.1%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

Using similar reaction conditions as described in step-iii of example-1, tert-butyl 4-(4-(6-cyclopropyl-3-(1-(3-fluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperazine-1-carboxylate (111 mg, 0.14 mmol) was hydrolyzed by lithium hydroxide (17.6 mg, 0.42 mmol), in methanol/water (3/2 ml) to afford 14 mg of the titled compound. 1H NMR (CDCl3, 300 MHz): δ 8.7 (b, 1H), 7.52 (s, 1H), 7.40-7.37 (m, 2H), 7.107-7.099 (d, 1H), 7.002-6.9 (m, 3H), 6.9-6.8 (m, 1H), 5.26 (s, 2H), 3.62-3.59 (t, 3H), 3.209-3.117 (t, 3H), 2.22 (s, 1H), 3.12 (s, 3H), 1.496 (s, 9H), 1.16-1.15 (m, 2H), 0.91-0.87 (m, 2H). MS: m/z=621.3 (M+1).

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-0c2636bc2c68409f942e02b23249a232
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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