Tetrahydrofuran → Methyl 2-[2-{[((1R*,2S*)-2-{[(5-chloroindol-2-yl)carbonyl]amino}cyclohexyl)amino]carbonyl}-6,7-dihydrothiazolo[5,4-c]pyridin-5(4H)-yl]ethylcarbamate Hydrochloride

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Reaction Steps

The compound (144 mg) obtained in Example 40 was dissolved in pyridine (3 mL), triethylamine (138 μl) was added, and the mixture was stirred at room temperature for 5 minutes. A solution prepared by adding triphosgene (49 mg) to tetrahydrofuran (1 mL) containing methanol (20 μl) was added dropwise to this solution at room temperature. After stirring for 1 hour, the reaction mixture was concentrated under reduced pressure, and the residue was dissolved in a 9:1 mixture of methylene chloride and methanol. Water was added to the solution for partitioning the mixture. The organic layer was separated and dried over sodium sulfate anhydrate. The solvent was distilled away under reduced pressure, and the residue was purified by silica gel column chromatography (methylene chloride:methanol=100:3) to give a colorless foamy substance. This product was suspended in 1N hydrochloric acid (0.2 mL), and the suspension was concentrated under reduced pressure to give the title compound (60 mg).

Provenance & Evidence