(1,3)Thiazolo(4,5-c)pyridin-2-amine → HCID 172930627, compound

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Reaction Steps

A mixture of diphenylmethyl 7-[(Z)-2-(1-t-butoxycarbonylcyclobut-1-oxyimino)-2-(2-tritylaminothiazol-4-yl)acetamido]-3-(3-iodo-1-propen-1-yl)-3-cephem-4-carboxylate (X-5', 641 mg, 0.58 mmole) and 2-aminothiazolo[4,5-c]pyridine (97 mg, 0.64 mmole) in dimethylsulfoxide (10 ml) was stirred at room temperature for 1 hour. The reaction mixture was diluted with ethyl acetate (150 ml), washed with water (2×150 ml), dried over sodium sulfate and concentrated under reduced pressure. The oily residue was triturated with diisopropyl ether and the resulting precipitate (558 mg) was treated with a mixture of 90% trifluoroacetic acid (10 ml) and anisole (2 ml) at room temperature for 1 hour. Concentration of the mixture followed by trituration of the residue with ether gave 313 mg of crude I-5C, which was purified by column chromatography [HP-20, eluted with 30% and 50% CH3OH: the packing in the PrepPAK-500/C18 (Waters), eluted with 10% CH3OH] to give 40 mg (11%) of I-5C. M.p. >150° C. (dec.).

Provenance & Evidence