Hydrochloric Acid → HCID 89650662, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of 4,6-dichloro-N-(3-pyridyl)pyridine-3-carboxamide (500 mg, 1.9 mmol) in EtOH (5 mL) was added ethyl 4-aminobenzoate (340 mg, 2.1 mmol) and HCl (0.1 mL, 4M). The mixture was heated in a microwave for 10 min at 100° C. then heated again at 130° C. for 20 min. More ethyl 4-aminobenzoate (100 mg, 0.6 mmol) was added and the mixture heated again at 130° C. for 20 min. The mixture was evaporated to dryness and the residue purified by flash chromatography (40 g Reveleris silica cartridge, 0-10% MeOH in DCM) to afford ii as an off white solid (334 mg, 46%). A 10 mg sample of ii was dissolved in DMSO and purified further using reverse phase preparatory HPLC (20-60% MeCN in water, 0.1% formic acid) to afford 8.74 mg of ii as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 8.85 (d, J=2.2 Hz, 1H), 8.65 (s, 1H), 8.33 (d, J=3.7 Hz, 1H), 8.11 (ddd, J=8.3, 2.5, 1.5 Hz, 1H), 7.96 (d, J=8.6 Hz, 2H), 7.40 (dd, J=8.1, 4.4 Hz, 3H), 7.15 (s, 1H), 4.30 (q, J=7.1 Hz, 2H), 1.32 (t, J=7.1 Hz, 31-1). [M+H]+ m/z=397.09.

Provenance & Evidence