Triethylamine → 3-(3-Chloro-2-methyl-benzylamino)-4-(1,1-dimethyl-propylamino)-cyclobut-3-ene-1,2-dione

Participants

Reaction Steps

Tetrahydrofuran (10 mL), 3-butoxy-4-(1,1-dimethyl-propylamino)-cyclobut-3-ene-1,2-dione (1,20 g, 5.0 mmol, Example 3), 3-chloro-2-methylbenzylamine hydrochloride (0.96 g, 5.0 mmol, Example 96, Step 1), and triethylamine (0.51 g, 5.0 mmol) were stirred together at room temperature for 65 hours. Processing the reaction mixture as in Example 96, Step 2 provided 1.44 g of a white solid. Two recrystallizations of the crude product from methanol gave 1.12 g of the title compound as a fluffy, white solid: mp 236°-237° C. (softens 233° C.). MS (m/z) 321/323 ([M+H]+). HPLC indicates a major component (99.6%).

Provenance & Evidence