HCID 13237005, compound → HCID 86702430, compound

Participants

Reaction Steps

A mixture of 3-(dimethylamino)-1-(2-methyl-3-furanyl)-2-(2-pyridinyl)-2-propen-1-one (205 mg, 0.8 mmol) and hexahydro-1H-azepine-1-carboximidamide hydrochloride (213 mg, 1.200 mmol) in ethanol (4 ml) was stirred at room temperature. Potassium tert-butoxide (180 mg, 1.600 mmol) was added and the mixture was heated at reflux for 45 minutes. After cooling to room temperature the reaction mixture was diluted with water and extracted with ethyl acetate. The organic extracts were combined, washed with water and brine, dried and evaporated. The residue was purified by mass-directed automated HPLC. The product was dissolved in a mixture of dichloromethane (2 ml) and methanol (0.5 ml) and hydrogen chloride (1M in ether, 0.5 ml) was added and the solvent was evaporated. The residue was co-evaporated with ether and triturated with ether. The solid was collected and dried to give the title compound (67 mg, 23%). LC/MS [M+H]+=335. 1H NMR (400 MHz, d6-DMSO): δ 8.74 (2H, d), 8.54 (1H, s), 8.12-8.10 (1H, m), 7.65-7.55 (2H, m), 7.43 (1H, d), 5.74 (1H, d), 3.84-3.80 (4H, m), 2.41 (3H, s), 1.85-1.70 (4H, m), 1.60-1.48 (4H, m).

Provenance & Evidence