Triethylamine → HCID 59646781, compound

Participants

Reaction Steps

A mixture of 3-(benzyloxy)-9,9-dimethyl-4-oxo-4,6,7,9-tetrahydropyrimido[2,1-c][1,4]oxazine-2-carboxylic acid (0.200 g, 0.605 mmol) and (2-methylthiazol-5-yl)methanamine dihydrochloride salt (0.135 g, 0.67 mmol) in acetonitrile (15 ml) was treated at 25° C. with triethylamine (0.40 ml, 2.9 mmol) followed by benzotriazole-1-yl-oxy-tris-(dimethylamino)-phosphoniumhexafluorophosphate (0.30 g, 0.68 mmol). After 3 hours, the reaction mixture was diluted with ethyl acetate, washed successively with saturated sodium bicarbonate and brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. Chromatography of the residue on silica gel (elution ethyl acetate) followed by crystallization from ethyl acetate gave 0.246 g (92% yield) of the title amide as white crystals; mp 167° C. 1HNMR 400 MHz (CDCl3) δ (ppm): 1.64 (6H, s, 2×CH3), 2.70 (3H, s, CH3), 4.0-4.08 (4H, m, 2×CH2), 4.68 (2H, d, J=5.8 Hz, NCH2), 5.32 (2H, s, OCH2), 7.34-7.39 (3H, m, aromatics), 7.49 (1H, s, CH), 7.50-7.53 (2H, m, aromatics), 7.72 (1H, broad t, NH). Anal. Calcd for C22H24N4O4S: C, 59.98; H, 5.49; N, 12.71; Found: C, 59.99; H, 5.31; N, 12.61.

Provenance & Evidence