Dimethylformamide → Morpholino 3-(5-cyclopropyl-1,2,4-oxadiazol-3-yl)imidazo[1,5-a]quinoline-5-carboxamide

Participants

Reaction Steps

To morpholino 2-hydroxyquinoline-4-carboxamide (VI, Step I, 0.47 g) in THF (15 ml) and dry DMF (2 ml) cooled at -15° is added potassium tert-butoxide in THF (1 M, 1.82 ml). The mixture is stirred for 15 min, after which p-toluenesulfonyl chloride (0.347 g) is added. After stirring for 40 min, 5-cyclopropyl-3-isocyanomethyl-1,2,4-oxadiazole (IX, 0.300 g) is added, followed by potassium tert-butoxide (1 M, 2.00 ml). The mixture is stirred an for additional 2 hr, quenched with several drops of aqueous sodium bicarbonate, and taken to dryness under reduced pressure. The residue is chromatographed (silica gel; methanol/ dichloromethane (2/98)) to give the product, which is crystallized from dichloromethane/ether/hexane to give the title compound, mp 250-252°; MS (m/z) at 389; IR 1628, 1584, 1115, 1249 and 1274 cm-1.

Provenance & Evidence