Carbamate → 5-(Quinolin-5-ylcarbamoyl)-4,5,6,7-tetrahydro-thiazolo[5,4-c]pyridine-2-carboxylic acid

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Reaction Conditions

Reaction Steps

5-tert-butyl 2-ethyl 6,7-dihydro[1,3]thiazolo[5,4-c]pyridine-2,5(4H)-dicarboxylate obtained in step V of example 1 was deprotected to get the hydrochloride salt of 4,5,6,7-Tetrahydro-thiazolo[5,4-c]pyridine-2-carboxylic acid ethyl ester. To a solution of a HCl salt of 4,5,6,7-Tetrahydro-thiazolo[5,4-c]pyridine-2-carboxylic acid ethyl ester (1.0 eq) in DMF was added Et3N (1.0 eq.) followed by carbamate derivative of Isoquinoline (1.0 eq) obtained in step I above. The reaction mixture was refluxed for 3 h at 90° C. Water was added and the organic layer was separated, dried over anhydrous Na2SO4 and concentrated under reduced pressure to afford crude product, which, was hydrolysed by stirring in MeOH: water and K2CO3 (2.0 eq.) for 48 h Reaction mixture was concentrated under reduced pressure and neutralized to pH 7.0 to afford 5-(Quinolin-5-ylcarbamoyl)-4,5,6,7-tetrahydro-thiazolo[5,4-c]pyridine-2-carboxylic acid).

Provenance & Evidence