Triethylamine → HCID 10347100, compound

Participants

Reaction Steps

A mixture of 6-chloro-9-(4-chlorophenyl)-8-(2-chlorophenyl)-9H-purine I-(4A-7)c (19 mg, 0.052 mmol), 1-isopropyl-1,3,8-triazaspiro[4.5]decan-4-one (Janssen, P. A. J., U.S. Pat. No. 3,238,216; 20 mg, 0.10 mmol) and triethylamine (11 μl) in ethanol (1 ml) was stirred overnight at room temperature. The reaction mixture was concentrated under reduced pressure and then purified on a Biotage™ Flash 12S column using 3% methanol in methylene chloride as eluant to afford title compound 13A-1 (25 mg): +ESI MS (M+1) 536.3; 1H NMR (400 MHz, CD3OD) δ 8.22 (s, 1H), 7.59 (d, J=7.5 Hz, 1H), 7.46–7.35 (m, 5H), 7.29 (d, J=8.7 Hz, 2H), 4.27 (s, 2H), 4.25 (v br s, 4H), 3.15 (septuplet, J=6.6 Hz, 1H), 2.00–1.83 (m, 4H), 1.07 (d, J=6.6 Hz, 6H). A solution of the material in methylene chloride/ methanol was treated with excess 1 N HCl in diethyl ether, stirred, evaporated to dryness, and then triturated in diethyl ether to afford the hydrochloride salt of compound 13A-1 (23 mg, 77%): 1H NMR (400 MHz, CD3OD) δ 8.43 (s, 1H), 7.61 (d, J=7.5 Hz, 1H), 7.53–7.40 (m, 5H), 7.35 (d, J=8.7 Hz, 2H), 4.20 (v br s), 3.94 (septuplet, J=6.6 Hz, 1H), 2.45 (m, 4H), 1.41 (d, J=6.6 Hz, 6H).

Provenance & Evidence