N-(6-amino-2,4-dioxo-7-trifluoromethyl-1,4-dihydro-2H-quinazolin-3-yl)-methanesulfonamide → HCID 11640324, compound

Participants

Reaction Steps

To a solution of 60 mg (0.18 mmol) of N-(6-amino-2,4-dioxo-7-trifluoromethyl-1,4-dihydro-2H-quinazolin-3-yl)-methanesulfonamide in 5 ml of acetic acid are added 26 mg (0.18 mmol) of 2,5-dimethoxy-3-methyl-tetrahydro-furan (prepared according to: Markwell, Roger Edward; Hadley, Michael Stewart; Blaney, Frank Edward. Azabicycloalkane derivatives and medicaments containing them. Eur. Pat. Appl. (1983) EP 95262 A1). The reaction mixture is stirred at reflux for 10 hours. Subsequently the solvents are evaporated and the crude product is purified by flash-master chromatography (cyclohexane/ethyl acetate, from 100/0 to 20/80) to yield N-[6-(4-methyl-2-oxo-2,3-dihydro-pyrrol-1-yl)-2,4-dioxo-7-trifluoromethyl-1,4-dihydro-2H-quinazolin-3-yl] methanesulfonamide. 1H-NMR ; DMSO-d6 (400 MHz, ppm):; 8.06 (s, 1H, aromatic); 7.60 (s, 1H , aromatic); 7.13 (m, 1H, N-CH═C(CH3)); 4.24 CO—CH2-C(s, 2CO—CH2-C(CH3)); 3.16 (s, 3H, S02-CH3); 1.84 (d, 3H, CH3) [M−H]-; Agilent LC/MSD 1100 Series, LC-MS method: Column: SunFireC18, 4.6*50 mm, 3.5 μm; negative MS; water/acetonitril 95:5 to 5:95 in 5 min, flow: 1.5 ml/min.

Provenance & Evidence