Triethylamine → HCID 69078773, compound

Participants

Reaction Steps

Tris(dibenzylideneacetone)dipalladium(0) chloroform adduct (0.12 mg, 0.03 eq.), 2-iodopyrazine (0.90 g, 1.1 eq), triethylamine (1.21 g, 3 eq.), and copper (I) iodide (46 mg, 0.06 eq.) were added sequentially to a solution of 2-ethyl-1-(2-propynyl)-1H-imidazo[4,5-c]quinolin-4-amine (1 g, 4 mmol, 1.0 eq.) in DMF. The reaction mixture was stirred at ambient temperature overnight. The reaction mixture was concentrated under reduced pressure to provide crude product which was purified by column chromatography (silica gel eluting with 8/92 methanol/dichloromethane). The residue was purified by recrystallization from DMF to provide 100 mg of 2-ethyl-1-[3-(pyrazin-2-yl)-2-propynyl]-1H-imidazo[4,5-c]quinolin-4-amine hydroiodide as tan granules, mp 180-225° C. (dec). 1H NMR (300 MHz, DMSO-d6) δ 13.31 (s, 1H), 8.70 (br s, 2H), 8.68 (d, J=1.4 Hz, 1H), 8.61 (m, 2H), 8.48 (dd, J=8.2, 0.9 Hz, 1H), 7.85 (d, J=8.2 Hz, 1H), 7.73 (m, 1H), 7.62 (m, 1H), 5.93 (s, 2H), 3.14 (q, J=7.4 Hz, 2H), 1.43 (t, J=7.4 Hz, 3H); MS (APCI) m/z 329 (M+H)+; Anal. calcd. for C19H16N6.HI.0.06 DMF: C, 50.01; H, 3.81; N, 18.43. Found: C, 49.96; H, 3.84; N, 18.15.

Provenance & Evidence