Oxalyl chloride → HCID 86628356, compound

Participants

Reaction Conditions

Reaction Steps

Oxalyl chloride (436 μL, 5 mmol) was carefully added dropwise, with stirring, to DMF (0.5 ml) at 0° C. then held for 25 minutes. A solution of cis-2,2,2-trifluoro-N-(1,2,3,4,10,14b-hexahydro-10-methyldibenzo[b,f]pyrido[1,2-d][1,4]diazepin-2-yl)acetamide (9: R2=COCF3) (400 mg, 1.07 mmol) in DMF (2 ml) was added dropwise to the resulting suspension and the reaction mixture heated to 80° C. and held for 1.5 hours. The reaction was cooled to ambient temperature and quenched by dropwise addition of NaHCO3 solution in H2O. The product was extracted into EtOAc, dried (Na2SO4) and concentrated under reduced pressure. Then the crude product was purified by column chromatography on silica to afford cis-2,2,2-trifluoro-N-(8-formyl-1,2,3,4,10,14b-hexahydro-10-methyldibenzo[b,f]pyrido[1,2-d][1,4]diazepin-2-yl)acetamide (9: R2=COCF3; R8=CHO) (130 mg, 30%). Data: (m/z)=404 (M+H)+. [Column chromatography also afforded cis-2,2,2-trifluoro-N-(6-formyl-1,2,3,4,10,14b-hexahydro-10-methyldibenzo[b,f]pyrido[1,2-d][1,4]diazepin-2-yl)acetamide (9: R2=COCF3; R6=CHO) (45 mg, 10%). Data: (m/z)=404 (M+H)+.]

Provenance & Evidence