Pyridine → HCID 49839675, compound

Participants

Reaction Steps

To a solution of N-(2-amino-pyridin-4-yl)-2,6-dichloro-benzamide (281 mg, 1.0 mmol) in anhydrous THF (5 mL) were added pyridine (97 μL, 1.2 mmol) and phenyl chloroformate (138 μL, 1.1 mmol). The reaction mixture was stirred at room temperature for 1 hr and then 3-methoxy propylamine (123 μL, 1.2 mmol) was added. The reaction mixture was stirred for 1 hr then partitioned between EtOAc (10 mL) and water (10 mL). The organic layer was washed with 1 N HCl, water and brine, dried over sodium sulfate, and concentraged under reduced pressure. The residue was purified by silica gel column chromatography (EtOAC/cyclohexane: gradient 0% to 100%) to give the desired compound (105 mg, yield: 26%). NMR (400 MHz, DMSO-d6): δ 11.09 (br s, 1H), 9.18 (br s, 1H), 8.20 (br s, 1H), 8.09 (d, J=5.7 Hz, 1H), 7.69 (d, J=1.8 Hz, 1H), 7.57-7.58 (m, 2H), 7.51 (dd, J=9.2, 6.8 Hz, 1H), 7.24 (dd, J=5.7, 1.9 Hz, 1H), 3.37 (t, J=6.2 Hz, 2H), 3.24 (s, 3H), 3.21-3.19 (m, 2H), 1.69 (m, 2H). LCMS (ESI) m/z: 397, 399 [M+H]+.

Provenance & Evidence