Boron trifluoride etherate → 2-(4-Methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-3,4,6,7-tetrahydro-imidazo[4,5-c]pyridine-5-carboxylic acid tert-butyl ester

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Reaction Steps

In accordance with scheme 8,4-methoxy-7-morpholin-4-yl-benzothiazole-2-carbothioic acid amide (XX) and iodomethane in tetrahydrofurane were stirred at room temperature for three days. The resulting precipitate was filtered to yield 4-methoxy-7-morpholin-4-yl-benzothiazole-2-carboximidothioic acid methyl ester hydroiodide. To a solution of 4-methoxy-7-morpholin-4-yl-benzothiazole-2-carboximidothioic acid methyl ester hydroiodide in tetrahydrofurane was added 3-amino-4,4-diethoxy-piperidine-1-carboxylic acid tert-butyl ester (XXVI) and the mixture was stirred at room temperature for two days. Then boron trifluoride etherate was added and the solvent is distilled off under vacuum. Again boron trifluoride etherate was added and the mixture was dissolved in dimethylformamide and heated for 10 minutes at 125° C. It was obtained 2-(4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-3,4,6,7-tetrahydro-imidazo[4,5-c]pyridine-5-carboxylic acid tert-butyl ester (Id2).

Provenance & Evidence