Triethylamine → HCID 58739064, compound

Participants

Reaction Steps

A mixture of 2-(1,1-dioxo-1λ6-[1,2]thiazinan-2-yl)-5-methoxy-1-methyl-6-oxo-1,6-dihydro-pyrimidine-4-carboxylic acid (0.235 g, 0.74 mmol) and 4-fluorobenzylamine (0.14 g, 1.13 mmol) in acetonitrile (10 ml) was treated at 22° C. with triethylamine (0.32 ml, 2.3 mmol) followed by benzotriazole-1-yloxy-tris-pyrrolidino-phosphonium hexafluorophosphate (0.42 g, 0.81 mmol) and the resulting mixture was stirred for 3 h. The reaction mixture was then diluted with ethyl acetate, washed with saturated sodium bicarbonate, brine and dried over anhydrous magnesium sulfate. Evaporation of the solvent and chromatography of the residue on silica gel (elution toluene-ethyl acetate 1:1 to ethyl acetate) gave 0.291 g (92% yield) of the title amide as a white solid. 1HNMR 400 MHz (CDCl3) δ (ppm): 1.6–1.7 and 2.3–2.5 (4H, m, 2×CH2), 3.2 and 3.5 (2×1H, m, CH2), 3.62 (3H, s, NCH3), 3.7 and 3.95 (2×1H, m, CH2), 4.04 (3H, s, OCH3), 4.59 (2H, d, J=5.8 Hz, NCH2), 7.04 (2H, m, aromatics), 7.31 (2H, m, aromatics), 7.75 (1H, broad, NH). HRMS (FAB POS) calculated for C18H22FN4O5S [M+H+]: 425.129495. found: 425.129040.

Provenance & Evidence