Hydrochloric Acid → 1-(2-Ethyl-cyclohexyl)-2-thiophen-2-ylmethyl-1H-benzoimidazole-5-carboxylic acid

HRID 1750251Notes

Reaction equation

C[O:2][C:3](=[O:28])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH:12]2[CH2:17][CH3:18])=[C:6]([NH:19][C:20](=O)[CH2:21][C:22]2[S:23][CH:24]=[CH:25][CH:26]=2)[CH:5]=1.Cl.O>O1CCOCC1>[CH2:17]([CH:12]1[CH2:13][CH2:14][CH2:15][CH2:16][CH:11]1[N:10]1[C:7]2[CH:8]=[CH:9][C:4]([C:3]([OH:2])=[O:28])=[CH:5][C:6]=2[N:19]=[C:20]1[CH2:21][C:22]1[S:23][CH:24]=[CH:25][CH:26]=1)[CH3:18]

Participants

Conditions

Temperature: 130 °C

Procedure

0.59 g 4-(2-Ethyl-cyclohexylamino)-3-(2-thiophen-2-yl-acetylamino)-benzoic acid methyl ester were reacted with 10 ml of 4M hydrochloric acid in dioxane at 130° C. in a microwave reactor for 20 min. 1 ml water was added and the mixture was heated to 130° C. for 30 min. The reaction was concentrated and the residue purified by chromatography (silica, ethyl acetate/heptane) to yield 0.47 g (88%) of 1-(2-Ethyl-cyclohexyl)-2-thiophen-2-ylmethyl-1H-benzoimidazole-5-carboxylic acid.

Workup

concentrationThe reaction was concentrated
customthe residue purified by chromatography (silica, ethyl acetate/heptane)

Sources & evidence

ORD record: ord-18e9ee8a946f4006aa63e60beb2321bd
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09156796B2

Reaction notes

Loading…