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

HRID 1788607Notes

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

Participants

Conditions

Temperature: 75 °C

Procedure

1-(4′-Chloro-4-chloro-biphen-2-yl)-ethanone (132 mg, 0.5 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 132 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-d05b9a35d6b640619d0c5b71820127fe
Source dataset: uspto-grants-2009_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07511145B2

Reaction notes

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