Lithium Hydroxide → Gsk-2636771

HRID 44508Notes

Reaction equation

[Li+].[OH-].[CH3:3][C:4]1[N:8]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[C:11]=2[CH3:20])[C:7]2[CH:21]=[C:22]([N:29]3[CH2:34][CH2:33][O:32][CH2:31][CH2:30]3)[CH:23]=[C:24]([C:25]([O:27]C)=[O:26])[C:6]=2[N:5]=1>C1COCC1>[CH3:3][C:4]1[N:8]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([F:18])([F:17])[F:19])[C:11]=2[CH3:20])[C:7]2[CH:21]=[C:22]([N:29]3[CH2:30][CH2:31][O:32][CH2:33][CH2:34]3)[CH:23]=[C:24]([C:25]([OH:27])=[O:26])[C:6]=2[N:5]=1

Participants

Conditions

Temperature: 50 °C

Procedure

An aqueous solution of 2 N LiOH (1.2 mL) was added to a solution of methyl 2-methyl-1-{[2-methyl-3-(trifluoromethyl)phenyl]methyl}-6-(4-morpholinyl)-1H-benzimidazole-4-carboxylate, prepared as described in Example 30 (180 mg, 0.4 mmol) in THF (10 mL) and stirred at 50° C. for 1 h. When TLC showed no starting material remaining, the mixture was cooled to rt and THF was removed under reduced pressure. The pH of the mixture was acidified to pH 3. The suspension was filtered and the filtrate was collected, and washed with water (10 mL) to give the product as a white solid (152 mg, yield 88%). 1H NMR (300 MHz, DMSO-d6): δ ppm 2.46 (s, 3H), 2.54 (s, 3H), 3.10 (t, 4H, J=4.8 Hz), 3.73 (t, 4H, J=4.8 Hz), 5.63 (s, 2H), 6.37 (d, 1H, J=7.8 Hz), 7.26 (t, 1H, J=7.8 Hz), 7.35 (d, 1H, J=2.4 Hz), 7.44 (d, 1H, J=2.4 Hz), 7.62 (d, 1H, J=7.8 Hz); LC-MS: m/e=434 [M+1]+.

Workup

customprepared
temperaturethe mixture was cooled to rt
customTHF was removed under reduced pressure
filtrationThe suspension was filtered
customthe filtrate was collected
washwashed with water (10 mL)

Sources & evidence

ORD record: ord-f5a2552e717e4ea9b42bd1be68e1060b
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08541411B2

Reaction notes

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