Diisopropylethylamine → 1-(4-Cyclopropylbuta-1,3-diyn-1-yl)-4-{[1-methoxy-3-(methylamino)-1,3-dioxopropan-2-yl](methyl)carbamoyl}benzene

Participants

Reaction Steps

HATU (1.1 g) and DIPEA (1.0 mL) were added to a DMF (4.0 mL) solution of 4-(4-cyclopropylbuta-1,3-diyn-1-yl)benzoic acid (0.42 g) as obtained in Example 6-(2), whereafter the mixture was stirred for 2.5 hours at room temperature. Then, N,N2,O-trimethyl-3-oxoserinamide hydrochloride (Intermediate 5-2, 0.59 g) was added, and the mixture was stirred for 40 minutes at 70 to 80° C. The reaction mixture was cooled to room temperature, and ethyl acetate and water were added to isolate the organic layer. The extract was washed sequentially with water and brine, and dried over anhydrous magnesium sulfate. The desiccant was filtered out, and then the solvent was distilled off under reduced pressure to obtain 1-(4-cyclopropylbuta-1,3-diyn-1-yl)-4-{[1-methoxy-3-(methylamino)-1,3-dioxopropan-2-yl](methyl)carbamoyl}benzene (brown oil) (0.81 g).

Provenance & Evidence