1,2-Dichloroethane → HCID 43089866, compound

Participants

Reaction Conditions

Reaction Steps

Combined 6-chloronicotinic acid (6.0 g, 38.1 mmol), HOBT (2.57 g, 19.04 mmol) and EDC (10.95 g, 57.1 mmol) in CH2Cl2 (100 mL) the Hunig's base (9.98 mL, 57.1 mmol) and 3-methoxypropan-1-amine (5.85 mL, 57.1 mmol) were added and stirred at 20° C. for 22 h. The reaction mixture was concentrated in vacuo to give a residue which was taken up in EtOAc (250 mL) and washed with saturated aqueous ammonium chloride (250 mL) and brine, dried over magnesium sulfate and concentrated in vacuo to give a residue which was purified on an 330 g silica gel column eluted with 10 to 80% EtOAc in hexanes to give the title compound (6.6 g, 76% yield) as a white solid. MS m/z 229, 231 [M+H]+. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.76 (quin, J=6.7 Hz, 2 H) 3.24 (s, 3 H) 3.27-3.35 (m, 2 H) 3.38 (t, J=6.3 Hz, 2 H) 7.65 (dd, J=8.3, 0.8 Hz, 1 H) 8.23 (dd, J=8.3, 2.5 Hz, 1 H) 8.73 (t, J=5.3 Hz, 1 H) 8.82 (dd, J=2.5, 0.8 Hz, 1 H).

Provenance & Evidence