Hydrochloric Acid → HCID 68386741, compound

HRID 1051184Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([CH:33]=[CH:34][CH:35]=1)[O:5][C:6]1[CH:7]=[C:8]([NH:26][CH2:27][CH2:28][C:29]([F:32])([F:31])[F:30])[C:9]2[N:13]=[CH:12][N:11]([C:14]3[CH:23]=[CH:22][C:17]([C:18]([O:20]C)=[O:19])=[C:16]([CH3:24])[CH:15]=3)[C:10]=2[CH:25]=1.CO.[OH-].[Li+].Cl>O1CCCC1.O>[F:1][C:2]1[CH:3]=[C:4]([CH:33]=[CH:34][CH:35]=1)[O:5][C:6]1[CH:7]=[C:8]([NH:26][CH2:27][CH2:28][C:29]([F:31])([F:32])[F:30])[C:9]2[N:13]=[CH:12][N:11]([C:14]3[CH:23]=[CH:22][C:17]([C:18]([OH:20])=[O:19])=[C:16]([CH3:24])[CH:15]=3)[C:10]=2[CH:25]=1

Participants

Conditions

Temperature: 23 °C

Procedure

To a solution of 275 mg (564 μmol) methyl 4-{6-(3-fluorophenoxy)-4-[(3,3,3-trifluoropropyl)amino]-1H-benzimidazol-1-yl}-2-methylbenzoate which was prepared according to intermediate example 10b in 12 mL tetrahydrofurane and 4 mL methanol were added 2.8 mL of a 1M aqueous lithium hydroxide solution and the mixture was stirred at 23° C. overnight. Water was added, the mixture was acidified by the addition of a 1M hydrochloric acid and extracted with dichloromethane and methanol. The organic layer was washed with brine and dried over sodium sulfate. After filtration and removal of solvent the residue was purified by chromatography to give 246 mg (88%) of the title compound.

Workup

extractionextracted with dichloromethane and methanol
washThe organic layer was washed with brine
dry with materialdried over sodium sulfate
filtrationAfter filtration and removal of solvent the residue
customwas purified by chromatography

Sources & evidence

ORD record: ord-6ee93dea489e4c0d9dc143a1be7b80ee
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09388140B2

Reaction notes

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