Methyl 4-((tert-butoxycarbonyl)amino)nicotinate → Methyl 4-aminopyridine-3-carboxylate

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Reaction Steps

Formula 505 where R1, R3 and R4 are H; W, Y and Z are —C═; and X is —N═: 4-tert-Butoxycarbonylamino-nicotinic acid methyl ester (9.08 g, 36.0 mmol) was dissolved in 50/50 TFA/DCM (100 mL) solution and stirred for 2 hours at room temperature. Concentration of the mixture under reduced pressure was followed by re-dissolution in DCM (100 mL), washing with saturated sodium bicarbonate, drying over sodium sulfate, and concentration under reduced pressure. The corresponding de-protected product of Formula 505, 4-amino-nicotinic acid methyl ester (5.43 g, 99.1%) was obtained was obtained in sufficient purity to be carried forward for use in the next step. MS (Cl) M/E: 153.1.

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