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

HRID 1788584Notes

Reaction equation

[Cl:1][C:2]1[CH:19]=[CH:18][C:5]([C:6]2[C:11]([C:12](=O)[CH3:13])=[CH:10][C:9]([N+:15]([O-:17])=[O:16])=[CH:8][CH:7]=2)=[CH:4][CH:3]=1.C([O:22][C:23]([C:25]1[CH:48]=[CH:47][C:28]2[N:29]([CH:41]3[CH2:46][CH2:45][CH2:44][CH2:43][CH2:42]3)[C:30]([C:32]3[CH:37]=[CH:36][C:35]([NH2:38])=[C:34]([CH:39]=O)[CH:33]=3)=[N:31][C:27]=2[CH:26]=1)=[O:24])C.[OH-].[K+].Cl>C(O)C>[Cl:1][C:2]1[CH:19]=[CH:18][C:5]([C:6]2[C:11]([C:12]3[CH:13]=[CH:39][C:34]4[C:35](=[CH:36][CH:37]=[C:32]([C:30]5[N:29]([CH:41]6[CH2:42][CH2:43][CH2:44][CH2:45][CH2:46]6)[C:28]6[CH:47]=[CH:48][C:25]([C:23]([OH:24])=[O:22])=[CH:26][C:27]=6[N:31]=5)[CH:33]=4)[N:38]=3)=[CH:10][C:9]([N+:15]([O-:17])=[O:16])=[CH:8][CH:7]=2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 75 °C

Procedure

1-(4′-Chloro-4-nitro-biphen-2-yl)-ethanone (69 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 34 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-4f538b2ec01b4155a5f2694438a7c789
Source dataset: uspto-grants-2009_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07511145B2

Reaction notes

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