Diisopropylethylamine → HCID 71208298, compound

Participants

Reaction Steps

Ethyldiisopropylamine (1.38 mL) and 2-chloro-5-ethylpyrimidine (380 μL) are added to a solution of 4-(2-piperidin-4-yl-2,3-dihydro-benzofuran-5-yl)-benzoic acid methyl ester (0.90 g) in tetrahydrofuran (20 mL) and the reaction mixture is heated to reflux for 48 h. The solvent is evaporated after cooling to room temperature. Dichloromethane and water are added; the aqueous phase is separated and extracted with dichloromethane. The combined organic phases are dried over MgSO4 and the solvent is evaporated. The residue is mixed with methanol (20 mL) and 1 M aqueous sodium hydroxide solution (6.67 mL). The reaction mixture is stirred at 55° C. for 12 h. The solvent is evaporated after cooling to room temperature. Dichloromethane and water are added; the organic phase is separated and extracted with water. The combined aqueous phases were adjusted to pH 2 with 1 M hydrochloric acid. The title compound is collected by filtration and dried at 50° C. in vacuo. LC (method 8): tR=1.56 min; Mass spectrum (ESI+): m/z=430 [M+H]+.

Provenance & Evidence