Cyclohexylamine → HCID 19891245, compound

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Reaction Steps

In 50 ml of dry dimethylformamide was dissolved 12.3 g of 2-tert-butoxycarbonyl-1,2,3,4-tetrahydrobenzo[b]thieno[2,3-c]pyridine-carboxylic acid synthesized in Example 13, and 4.02 g of cyclohexylamine was further added thereto, followed by stirring for 30 minutes. Then 6.7 ml of triethylamine and a solution of 12.17 g of diphenylphosphorylazide in 10 ml of dry dimethylformamide were further added, and the resulting mixture was stirred at room temperature for one day. After dimethylformamide was distilled off under reduced pressure, the residue was dissolved in 300 ml of ethyl acetate, washed with 50 ml of an aqueous 5% sodium hydrogencarbonate solution three times, and then an aqueous 5% citric acid solution twice, and then a saturated aqueous sodium chloride solution twice, and then dried by sodium sulfate. Thereafter, ethyl acetate was distilled off under reduced pressure and the residue was purified by silica gel thin layer chromatography (developing solution: chloroform), whereby 9.17 g of N-cyclohexyl-2-tert-butoxycarbonyl-1,2,3,4-tetrahydrobenzo[b]thieno[2,3-c]pyridine-3-carboamide was obtained (yield 60%).

Provenance & Evidence