4-(Aminomethyl)-3-chlorobenzonitrile → 3-Chloro-4-{[3,4-dioxo-2-(1,2,2-trimethyl-propylamino)-cyclobut-1-enylamino]-methyl}-benzonitrile

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Reaction Steps

A solution of 3-butoxy-4-(1,2,2-trimethyl-propylamino)cyclobut-3-ene-1,2-dione (1.27 g, 5.0 mmol, Example 5), 2-chloro-4-cyanobenzylamine (0.833 g, 5.0 mmol, Example 2, Step 3) and tetrahydrofuran (8 mL) was stirred at room temperature for 23 hours, refluxed for 4 hours and allowed to stand at room temperature for approximately 62 hours. The mixture was freed of solvent and the residue was triturated with diethyl ether and dried. The resulting white solid (1.096 g) was recrystallized three times from methanol to yield 771 mg (45%) of the title compound as a faintly pink solid: mp 250.0°-251.5° C. (softens 248.0° C.); 1H NMR (DMSO-d6) δ8.10 (d, 1H), 7.88 (m, 1H), 7.70 (br m, 1H), 7.61 (d, 1H), 7.37 (br m, 1H), 4.88 (m, 1H), 3.91 (br m, 1H), 1.11 (d, 3H), 0.86 (s, 9H) ppm IR (KBr): 3200, 2230, 1790, 1635 cm-1 ; MS (m/z) 345/347 (M+). HPLC indicates a major component (98.7%).

Provenance & Evidence