1,2-Dichloroethane → HCID 22593808, compound

Participants

Reaction Steps

EDC (230 mg, 1.2 mmole) was added to a solution (E)-3-(6-aminopyridin-3-yl)acrylic acid (164 mg, 1.0 mmole), 2-(methylaminomethyl)thieno[3,2-b]thiophene (220 mg, 1.2 mmole), HOBt H2O (162 mg, 1.2 mmole), and Et3N (0.35 mL, 2.5 mmole) in dry DMF (5 mL) at RT. After 18 hr the mixture was diluted with H2O and extracted with EtOAc (3×). The combined organic layers were dried (MgSO4) and concentrated. The solid was taken up in 1:I MeOH/H2O and filtered. The filtrate was concentrated to approximately ⅓ volume. The precipitate was collected by filtration, washed with H2O, and died in vacuo to afford the title compound (139 mg, 42%) as a light tan solid: 1H NMR (400 MHz, d6-DMSO) δ 8.15 (d, J=2.0 Hz,1H), 7.83 (bd,1H), 7.61 (d, i=5.2 Hz, 1H), 7.40 (m, 3H), 6.45 (m, 2H), 4.75 (s, 2H), 3.13 (s, 3H); for minor rotomer δ5.00 (s, 2H), 2.95 (s, 3H); MS (ES) nm/e 330 (M+H)+.

Provenance & Evidence