Ethylenediamine → HCID 71512713, compound

Participants

Reaction Steps

To a solution of methyl 6-[2-(4-methoxyphenyl)-2-oxoethyl]-6H-thieno[2,3-b]pyrrole-5-carboxylate (100 mg, 0.30 mmol) in 1,4-dioxane (10 mL) was added ethylenediamine (0.78 mL, 12 mmol) and the mixture heated at reflux. The reaction was monitored by LCMS. Upon completion, the reaction mixture was concentrated in vacuo and the residue purified by flash chromatography (1 to 6% methanol-dichloromethane) to yield 11a-(4-methoxyphenyl)-2,3,11,11a-tetrahydro-1H,5H-imidazo[1,2-a]thieno[3′,2′:4,5]pyrrolo[1,2-d]pyrazin-5-one (75 mg, 73% yield) as a white solid. ESI-MI m/z [M+H]+ 340.25. 1H NMR (400 MHz, CDCl3) δ 7.31 (d, J=8.7 Hz, 2H), 7.14 (s, 1H), 6.96 (d, J=5.3 Hz, 1H), 6.82 (d, J=5.3 Hz, 1H), 6.78 (d, J=8.7 Hz, 2H), 4.52 (d, J=11.7 Hz, 1H), 4.25 (d, J=11.7 Hz, 1H), 4.02-3.89 (m, 1H), 3.73 (s, 3H), 3.64-3.51 (m, 1H), 3.37-3.26 (m, 1H), 3.08-2.94 (m, 1H).

Provenance & Evidence