Dimethylformamide → 2-(2-tert-Butoxycarbonylamino-phenylcarbamoyl)-1-methyl-1,4,5,7-tetrahydro-pyrrolo[2,3-c]pyridine-6-carboxylic acid tert-butyl ester

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Reaction Steps

To a solution of compound 6-(tert-butoxycarbonyl)-1-methyl-4,5,6,7-tetrahydro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid (1.0 eq) in DMF was added Dicyclohexyl carbo diimide (1.3 eq.) and hydroxy benzotriazole (1.3 eq) and reaction was stirred for 1 hr. followed by addition of monoboc protected phenylene diamine. The reaction was stirred further for 48 hrs. Water was added and reaction mixture was extracted with dichloromethane, dried over anhydrous sodium sulfate, concentrated under reduced pressure to afford crude product, which, on purification by column chromatography afforded the desired compound 2-(2-tert-Butoxycarbonylamino-phenylcarbamoyl)-1-methyl-1,4,5,7-tetrahydro-pyrrolo[2,3-c]pyridine-6-carboxylic acid tert-butyl ester which was treated with ethereal HCl to afford the hydrochloride salt of the base which was then neutralized to obtained the N-(2-aminophenyl)-1-methyl-4,5,6,7-tetrahydro-1H-pyrrolo[2,3-c]pyridine-2-carboxamide.

Provenance & Evidence