Lithium Hydroxide → Gsk-2636771

HRID 539187Notes

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-49b377a7ceff4789a32ec0e15436d803
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08865912B2

Reaction notes

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