Hydrochloric Acid → 2-[2-[2-(4-Chlorophenyl)-5-fluoro-phenyl]-6-quinolyl]-1-cyclohexyl-benzimidazole-5-carboxylic acid

HRID 1788605Notes

Reaction equation

[Cl:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]2[C:11]([C:12](=O)[CH3:13])=[CH:10][C:9]([F:15])=[CH:8][CH:7]=2)=[CH:4][CH:3]=1.C([O:20][C:21]([C:23]1[CH:46]=[CH:45][C:26]2[N:27]([CH:39]3[CH2:44][CH2:43][CH2:42][CH2:41][CH2:40]3)[C:28]([C:30]3[CH:35]=[CH:34][C:33]([NH2:36])=[C:32]([CH:37]=O)[CH:31]=3)=[N:29][C:25]=2[CH:24]=1)=[O:22])C.[OH-].[K+].Cl>C(O)C>[Cl:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]2[C:11]([C:12]3[CH:13]=[CH:37][C:32]4[C:33](=[CH:34][CH:35]=[C:30]([C:28]5[N:27]([CH:39]6[CH2:40][CH2:41][CH2:42][CH2:43][CH2:44]6)[C:26]6[CH:45]=[CH:46][C:23]([C:21]([OH:22])=[O:20])=[CH:24][C:25]=6[N:29]=5)[CH:31]=4)[N:36]=3)=[CH:10][C:9]([F:15])=[CH:8][CH:7]=2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 75 °C

Procedure

1-(4′-Chloro-4-fluoro-biphen-2-yl)-ethanone (62 mg, 0.25 mmol) and 2-(4-amino-3-formyl-phenyl)-1-cyclohexyl-1H-benzoimidazole-5-carboxylic acid ethyl ester (98 mg, 0.25 mmol) were dissolved in 500 μL ethanol and 500 μL 10% ethanolic KOH were added. The reaction was stirred at 75° C. overnight. The reaction was acidified with 4N hydrochloric acid, extracted three times with ethyl acetate, the organic extracts were dried with sodium sulfate and then evaporated. Purification via reverse-phase HPLC gave 84 mg product.

Workup

extractionextracted three times with ethyl acetate
dry with materialthe organic extracts were dried with sodium sulfate
customevaporated
customPurification via reverse-phase HPLC

Sources & evidence

ORD record: ord-8352f928c7e34d6bb53ce46f2706993e
Source dataset: uspto-grants-2009_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07511145B2

Reaction notes

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