Boron trifluoride etherate → HCID 22648164, compound

Participants

Reaction Steps

To a solution of 1-(2,6-dichlorophenyl)-5-(2-chlorophenyl)-7-(1-ethyl-2-oxoazepan-5-yl)-3,4-dihydro-2(1H)-quinazolinone (EXAMPLE 78) (9.7 mg, 0.018 mmol) in THF (0.2 mL) under N2 atmosphere was added BH3.THF (88 μL, 1.0M solution in THF). The reaction was stirred at RT overnight. The solvent was removed in vacuo, and the residue was dissolved in CH2Cl2. The resulting solution was washed with brine and dried over Na2SO4. After removal of the solvent in vacuo, the residue was re-dissolved in CH2Cl2 (0.5 mL) then cooled down to 0° C. To this was added Et3SiH (3 μL, 0.036 mmol) followed by BF3.Et2O (2.5 μL, 0.04 mmol), and the mixture was slowly warmed to RT over 2 hours. It was quenched with saturated solution of NaHCO3, then extracted with CH2Cl2 three times. The combined extracts were washed with brine and dried over Na2SO4. The crude residue was purified by preparative TLC eluting with 5% 2M NH3 in MeOH(CH2Cl2 to obtain 1-(2,6-Dichlorophenyl)-5-(2-chlorophenyl)-7-(1-ethylazepan-5-yl)-3,4-dihydro-2(1H)-quinazolinone. 1H NMR (CDCl3, 500 MHz): selected data δ 1.03 (t, J=7.1 Hz, 3H), 1.6-1.87 (m, 6H), 2.52 (q, J=7.1 Hz, 2H), 2.56-2.73 (m, 5H). MS(ES) 530 (M+H); LC 1: 2.36 min.

Provenance & Evidence