Hydrochloric Acid → Cyclopentylmethyl-1-(1-ethyl-propyl)-1H-benzoimidazole-5-carboxylic acid methyl ester
Reaction equation
[CH3:1][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][CH:19]2[CH2:23][CH2:22][CH2:21][CH2:20]2)[CH:5]=1.Cl>O1CCOCC1>[CH3:1][O:2][C:3]([C:4]1[CH:9]=[CH:8][C:7]2[N:10]([CH:11]([CH2:14][CH3:15])[CH2:12][CH3:13])[C:17]([CH2:18][CH:19]3[CH2:23][CH2:22][CH2:21][CH2:20]3)=[N:16][C:6]=2[CH:5]=1)=[O:25]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 140 °C
Procedure
2.93 g of 3-(2-Cyclopentyl-acetylamino)-4-(1-ethyl-propylamino)-benzoic acid methyl ester were dissolved in 7.5 ml of dry dioxane and 7.5 ml of 4M hydrochloric acid in dioxane were added. The reaction was heated in a microwave reactor to 140° C. for 30 min. The reaction mixture was concentrated, the residue was taken up in ethyl acetate, washed with saturated aqueous sodium bicarbonate solution, dried over magnesium sulphate and concentrated to yield 26.9 g (97%) of 2-Cyclopentylmethyl-1-(1-ethyl-propyl)-1H-benzoimidazole-5-carboxylic acid methyl ester as a brown solid which was used in the next step without further purification.
Workup
- concentrationThe reaction mixture was concentrated
- washwashed with saturated aqueous sodium bicarbonate solution
- dry with materialdried over magnesium sulphate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-adf97087d6144e6d8f57e77e84feed34
- Source dataset
- uspto-grants-2015_10
- Patent number
- US09156796B2
Reaction notes
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