Triethylamine → HCID 19367096, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 6-chloro-2-(chloromethyl)imidazo[1,2-α]pyridine (Example 4, step 1, 0.857 g), 3-fluoro-4-(piperazin-1-yl)benzonitrile (1.039 g), triethylamine (0.75 mL), and THF (6 mL) is stirred for 3 h at 75-80° C. The mixture is then concentrated under reduced pressure and the residue is partitioned between dichloromethane and saturated sodium bicarbonate. The combined organic layers are dried with MgSO4 and concentrated under reduced pressure. The residue is chromatographed on silica gel using methanol/dichloromethane (4/96). The appropriate fractions are combined and concentrated. Ethyl ether is added to the residue and the resulting solid is collected, washed with additional ethyl ether, and dried under reduced pressure to give 1.25 g of the title compound. A portion of this material is recrystallized from ethyl acetate; mp 132-133° C. ; IR (mineral oil) 1255, 1513, 1246, 801, 1504 cm-1 ; 1H NMR (CDCl3) δ2.74, 3.26, 3.77, 6.90, 7.13, 7.25, 7.34, 7.53, 8.13.

Provenance & Evidence