Ammonia → HCID 131727110, compound

Participants

Reaction Steps

0.188 g of the product obtained in Stage K of Example 1 is dissolved in 30 ml of dichloromethane, in a round-bottomed flask placed under an argon atmosphere at 0° C. 70 μl of diphosgene are added and then after 1 h 15 min 0.49 ml of a concentrated aqueous ammonia solution is added. After one hour, methylene chloride is added to the reaction medium and the organic phase is washed with an aqueous NaH2PO4 solution and then with an aqueous NaCl solution. The organic phases are dried over magnesium sulfate, filtered and the solvent is evaporated under reduced pressure. The crude product obtained is purified by chromatography on silica, eluting with a methylene chloride/ethyl acetate/triethylamine, 8/2/0.1%, mixture, and then next eluting with a dichloromethane/ethyl acetate/triethylamine, 7/3/0.1%, mixture. After evaporation of the fractions, 32 mg of the isomer A of compound methyl trans-1-(aminocarbonyl)-4,5,6,8-tetrahydro-6-oxo-5-(phenylmethoxy)-1H-4,7-methanopyrazolo[3,4-e][1,3]diazepine-8-carboxylate are obtained with a yield of 15%, and 79 mg of the isomer B of the compound methyl trans-2-(aminocarbonyl)-2,5,6,8-tetrahydro-6-oxo-5-(phenylmethoxy)-4H-4,7-methanopyrazolo[3,4-e][1,3]diazepine-8-carboxylate with a yield of 37%. The empirical formulae of the isomers are C17H17N5O5 (M=371.36 g).

Provenance & Evidence