Trifluoroacetic acid → HCID 59519003, compound

Participants

Reaction Steps

4-[2-(4-Fluoro-3-methoxyphenyl)-3-(isopropylcarbamoylmethyl)-4-oxo-3,4-dihydroquinazolin-6-yl]-2,6,6-trimethylperhydro-1,4-diazepine-1-carboxylic acid tert-butyl ester (120 mg, 0.197 mmol) was dissolved in DCM (6 mL) and TFA (3 mL) added. The reaction was stirred at room temperature for 4 h. Product mixture was poured directly onto an SCX cartridge and product eluted with 2N NH3/MeOH. Solvent was evaporated under reduced pressure to afford a red solid. Product was diluted with MeOH (20 mL) and heated at reflux temperature with activated carbon. The mixture was filtered through a celite pad, solvent evaporated under reduced pressure and the resultant product recrystallised from ethanol:heptane. This afforded 2-[2-(4-fluoro-3-methoxyphenyl)-4-oxo-6-(3,6,6-trimethylperhydro-1,4-diazepin-1-yl)-4H-quinazolin-3-yl]-N-isopropylacetamide (EXAMPLE 8a) (74 mg, 0.145 mmol, 74%). Data for 2-[2-(4-fluoro-3-methoxyphenyl)-4-oxo-6-(3,6,6-trimethylperhydro-1,4-diazepin-1-yl)-4H-quinazolin-3-yl]-N-isopropylacetamide (EXAMPLE 8a): MS (ESI) m/z: 510 ([M+H]+).

Provenance & Evidence