Imidazole → 4-Methoxy-7-morpholin-4-yl-benzothiazole-2-carbonitrile

Participants

Reaction Steps

In accordance with scheme 6, to a solution of 4-methoxy-7-morpholin-4-yl-benzothiazole-2-carboxylic acid (for R1=morpholinyl, XII) and imidazole in pyridine was added at 0° C. phosphoroxychloride. After about 5 hours, the cold solution was diluted with ethylacetate and worked up in conventional manner to obtain 4-methoxy-7-morpholin-4-yl-benzothiazole-2-carbonitrile (IXX), which was dissolved in triethylamine and in pyridine and was then stirred for 4 hours with hydrogen sulfide at room temperature. Solvent and excess hydrogen sulfide were removed. The obtained 4-methoxy-7-morpholin-4-yl-benzothiazole-2-carbothioic acid amide (XX) was dissolved in tetrahydrofurane and was reacted with iodomethane at 50° C. for about 4 hours. All volatile components were distilled off under vacuum and the residue was dissolved in a solution of 4,4-diethoxy-tetrahydro-pyran-3-ylamine in tetrahydrofurane. The mixture was stirred at 50° C. overnight, the solvent was distilled off and the residue was suspended in hydrochloric acid and stirred for about 3 hours at room temperature. It was obtained (4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-3,4,6,7-tetrahydro-pyrano[3,4-d]imidazole Id1).

Provenance & Evidence