Hydrochloric Acid → 1-Cyclohexyl-2-[2-(4-quinolyl)-6-quinolyl]benzimidazole-5-carboxylic acid

HRID 1788582Notes

Reaction equation

[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:11](=O)[CH3:12])=[CH:3][CH:2]=1.C([O:16][C:17]([C:19]1[CH:42]=[CH:41][C:22]2[N:23]([CH:35]3[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]3)[C:24]([C:26]3[CH:31]=[CH:30][C:29]([NH2:32])=[C:28]([CH:33]=O)[CH:27]=3)=[N:25][C:21]=2[CH:20]=1)=[O:18])C.[OH-].[K+].Cl>C(O)C>[N:32]1[C:29]2[C:28](=[CH:27][C:26]([C:24]3[N:23]([CH:35]4[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40]4)[C:22]4[CH:41]=[CH:42][C:19]([C:17]([OH:18])=[O:16])=[CH:20][C:21]=4[N:25]=3)=[CH:31][CH:30]=2)[CH:33]=[CH:12][C:11]=1[C:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[N:1]=[CH:2][CH:3]=1

Participants

Conditions

Temperature: 75 °C

Procedure

(1-Quinolin-4-yl-ethanone (43 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 then added. The reaction was stirred at 75° C. overnight. The reaction was acidified with 4N hydrochloric acid, extracted three times with ethyl acetate, and the organic extracts were dried with sodium sulfate and then evaporated. Purification via reverse-phase HPLC gave 24 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-4019479c4c134858b9dfdacc9546d653
Source dataset: uspto-grants-2009_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07511145B2

Reaction notes

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