Pyridine → HCID 71543161, compound

Participants

Reaction Conditions

Reaction Steps

5-Methoxypyrazine-2-carboxylic acid (0.438 g, 2.84 mmol) was dissolved in DMF (15.09 ml). Pyridine, anhydrous (0.492 ml, 6.04 mmol) was added followed by HATU (1.492 g, 3.92 mmol), and the mixture was stirred for 30 minutes, then cooled to 0° C., and (S)-2,7′-diamino-4′-fluoro-5,6-dihydrospiro[[1,3]thiazine-4,9′-xanthen]-2′-ol (1.0 g, 3.02 mmol) was added. The solution was stirred at 0° C. for 45 min, then allowed to warm to RT and stirred for additional 2 hrs. At this point, LCMS (117271-22-1) indicated complete conversion to the desired product with MS+=468 (M+1). No bis-amide was detected. Water was added to quench the reaction. The resulted suspension was stirred for 25 min, then filtered. The filter cake was rinsed with water a few times, and then dried in air affording (S)—N-(2-amino-4′-fluoro-2′-hydroxy-5,6-dihydrospiro[[1,3]thiazine-4,9′-xanthen]-7′-yl)-5-methoxypyrazine-2-carboxamide (1.2 g, 2.57 mmol, 85% yield) as red solid. MS m/z=468.0 [M+H]. This intermediate was carried on without purification.

Provenance & Evidence