Triethylamine → HCID 59164460, compound

Participants

Reaction Steps

To a solution of 2-amino-5-[5-methyl-2-(2-trimethylsilanylmethoxy-ethyl)-2H-pyrazol-3-yl]-4-trifluoromethyl-benzoic acid methyl ester (426 mg, 0.99 mmol) in DCM (10 mL) containing Et3N (0.55 mL, 4 equiv) was added (CCl3O)2CO (147 mg, 0.5 equiv) portionwise. The mixture was stirred at r.t. for 2 h and then concentrated in vacuo to dryness. The resulting paste was dissolved in THF (10 mL) and CH3SO2NHNH2 (109 mg, 1 equiv) was added. After stirring the mixture at r.t. for 1 h, an aqueous solution of NaOH (1N, 1 mL, 1 equiv) was added. The mixture was stirred for 2 h at r.t. Then, the mixture was poured into water and the aqueous phase was extracted with AcOEt (3 times). The organic phases were combined, dried (Na2SO4) and concentrated in vacuo to afford a crude solid. The crude product was purified by flash chromatography (hexanes to EtOAc/hexanes (3:1)) to provide N-{6-[5-methyl-2-(2-trimethylsilanylmethoxy-ethyl)-2H-pyrazol-3-yl]-2,4-dioxo-7-trifluoromethyl-1,4-dihydro-2H-quinazolin-3-yl}-methanesulfonamide (140 mg, 26%) as a yellow paste. (ESI-MS: m/z 534.6 [M+H]+, rt 5.69 min).

Provenance & Evidence