Triethylamine → HCID 178461763, compound

Participants

Reaction Steps

Dissolve (R)-[4-((E)-3,8-difluoro-6H-dibenzo[b,e]oxepin-11-ylidenemethyl)-2-nitro-phenyl]-(1-methyl-2-morpholin-4-yl-ethyl)-amine (0.017 mol, 9.0 g) in tetrahydrofuran (35 mL) and isopropanol (90 mL). Add triethylamine (0.039 mol, 3.9) and 10% platinum on carbon (1.5 g) and hydrogenate in a Parr shaker at 50 psi (H2) at room temperature for 2 h. Filter off the catalyst through a plug of diatomaceous earth. Dilute the filtrate with dioxane (35 mL), add diphenyl N-cyanocarbonimidate (0.019 mol, 4.61 g) and stir at room temperature for 48 h. Concentrate the reaction mixture under reduced pressure. Purify on a silica gel column using 0.5% methanol in dichloromethane as eluent to obtain the title compound (6.0 g, 64%) as an off-white solid. LC-MS m/z 528.2 [M+H]+.

Provenance & Evidence