Hydrochloric Acid → HCID 22184425, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 5-[3,5-bis(trifluoromethyl)benzyl]-9-chloro-7-(2-methylphenyl)-6-oxo-2,3,4,5-tetrahydro-6H-pyrido[2,3-b][1,5]oxazocine (compound of Reference Example 17; 100 mg) and 1-(t-butoxycarbonyl)homopiperazine (95.0 mg) was stirred at 150° C. for 5 hours. While the resulting residue was chilled on an ice bath, a 3 mol/L ethyl acetate solution of hydrogen chloride (1 mL) was added, and then the mixture was stirred at room temperature for 1 hour. The solvent was removed by distillation to obtain a residue, and then the residue was dissolved in tetrahydrofuran (1 mL). While the resulting solution was chilled on an ice bath, triethylamine (0.2 mL) and acetic anhydride (0.1 mL) were added, and then the mixture was stirred for 1 hour. To the reaction mixture, ethyl acetate was added. The resulting mixture was washed with water, and was then dried on anhydrous sodium sulfate. The solvent was removed by distillation to obtain a residue, and then the residue was purified on a silica gel column chromatography (ethyl acetate:methanol=10:1) to obtain 9-(4-acetylhomopiperazine-1-yl)-5-[3,5-bis(trifluoromethyl)benzyl]-7-(2-methylphenyl)-6-oxo-2,3,4,5-tetrahydro-6H-pyrido[2,3-b][1,5]oxazocine (42.7 mg, 36%).

Provenance & Evidence