Hydrochloric Acid → 1-(1-Ethyl-propyl)-2-isoxazol-5-ylmethyl-1H-benzoimidazole-5-carboxylic acid

HRID 1750215Notes

Reaction equation

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

Participants

Conditions

Temperature: 130 °C

Procedure

To 1.06 g 4-(1-Ethyl-propylamino)-3-(2-isoxazol-5-yl-acetylamino)-benzoic acid methyl ester were added 7.5 ml of 4M hydrochloric acid in dioxane. The reaction mixture was heated to 130° C. for 20 min in a microwave reactor. After cooling to rt 2 ml of water were added and the reaction was again heated to 130° C. for 20 min. The reaction was concentrated and the residue purified by chromatography (silica, ethyl acetate/heptane) to yield 0.85 g (90%) of 1-(1-Ethyl-propyl)-2-isoxazol-5-ylmethyl-1H-benzoimidazole-5-carboxylic acid.

Workup

additionwere added
temperaturethe reaction was again heated to 130° C. for 20 min
concentrationThe reaction was concentrated
customthe residue purified by chromatography (silica, ethyl acetate/heptane)

Sources & evidence

ORD record: ord-4fd4a4f87c504feb85b6c2dca72864f1
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09156796B2

Reaction notes

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