Water → N-(4-(2,6-dichlorobenzamido)pyridin-2-yl)thiophene-2-carboxamide

Participants

Reaction Conditions

Reaction Steps

N-(2-aminopyridin-4-yl)-2,6-dichlorobenzamide (240 mg, 0.86 mmol) was dissolved in pyridine (10 mL). The mixture was stirred at 0° C. for 20 min. and then thiophene-2-carbonyl chloride (113 mg, 0.77 mmol) was added dropwise. The mixture was warmed to 23° C. and stirred under nitrogen overnight. The next day, water (1 mL) was added and the mixture was stirred for 5 min. The reaction was concentrated under reduced pressure and the residue was purified by reverse-phase HPLC (Gemini, 200 mm×25 mm, gradient: CH3CN/0.05% NH3.H2O, 50-80, 10 min) to afford the desired product (72.6 mg, yield: 22%). 1HNMR: (DMSO-d6, 400 MHz): δ 11.38 (s, 1H), 10.92 (s, 1H), 8.47 (s, 1H), 8.33 (d, J=5.6 Hz, 1H), 8.26 (d, J=2.8 Hz, 1H), 7.90 (d, J=5.2 Hz, 1H), 7.62-7.51 (m, 4H), 7.22 (t, J=4.4 Hz, 1H). LCMS (ESI) (m/z): 414.3 [M+Na+].

Provenance & Evidence