Triethylamine → HCID 178521744, compound

Participants

Reaction Steps

To 260 mg (1.9 mmol) of 5-amino-3-cyclobutylpyrazole in 7 mL of acetonitrile was added 407 mg (1.9 mmol) of 2-trichloroacetylpyrrole and 220 μL of triethylamine. The mixture was stirred and heated at reflux, under nitrogen, for 12 hours. TLC analysis showed some starting material still remained. The mixture was concentrated and chromatographed over silica gel, eluting with 5% methanol in chloroform. The fractions containing the product were concentrated to an oil, which crystallized upon concentration from ether and methanol, to afford 200 mg (0.87 mmol, 46%) of a beige solid, m.p. 207–209° C., 1H NMR (DMSO-d6) δ 12.1 (s, 1H), 11.5 (s, 1H), 10.2 (s, 1H), 7.08 (s, 1H), 6.89 (s, 1H), 6.41 (s, 1H), 6.09 (s, 1H), 3.46 (m, 1H), 2.24 (m, 2H), 2.11 (m, 2H), 2.0–1.8 (m, 2H); IR (drift) 3329, 3294, 3257, 3225 (b), 2460 (w), 2351 (w), 2318 (w), 2257 (w), 1643 (s), 1588 (s), 1541, 1487 (s), 1416, 757, 747, cm−1 Anal. Calcd for C12H14N4O: C, 62.59; H, 6.13; N, 24.33. Found: C, 62.37; H, 6.22; N, 24.13.

Provenance & Evidence