1,1'-Carbonyldiimidazole → HCID 57415625, compound

Participants

Reaction Conditions

Reaction Steps

A solution of (2R,6S,13aS,14aR,16aS)-12,12-difluoro-6-(5-methylisoxazole-3-carboxamido)-5,16-dioxo-2-(phenanthridin-6-yloxy)octadecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclo pentadecine-14a-carboxylic acid (Example 18i, 21 mg, 0.030 mmol) and di(1H-imidazol-1-yl)methanone (10.96 mg, 0.068 mmol) in dichloroethane (400 μl) was stirred for 2 hr at 42° C. To this mixture was added methylsulfonylcyclopropane (11.0 mg, 0.091 mmol) and 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine (13.8 μl, 0.091 mmol) and the reaction mixture was stirred for 2 h at 42° C. The reaction mixture was diluted with ethyl acetate (7 mL) and washed with 10 mL of 1 N HCl followed by saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous sodium sulfate, filtered, and evaporated under reduced pressure. The resulting residue was purified by flash chromatography on silica gel (3% methanol/dichloromethane). The resulting material was further purified by reverse phase HPLC (40% acetonitrile/water with 0.1%TFA to 100% water) to provide the title compound N-((2R,6S ,13aS,14aR,16aS)-14a-(cyclopropylsulfonylcarbamoyl)-12,12-difluoro-5,16-dioxo-2-(phenanthridin-6-yloxy)octadecahydrocyclopropa[e]pyrrolo [1,2-a][1,4]diazacyclopentadecin-6-yl)-5-methylisoxazole-3-carboxamide (16 mg, 66.3% yield). MS (ESI): m/z=793.1 [M+H], 791.0 [M−H].

Provenance & Evidence