HCID 68540457, compound → HCID 68543984, compound

Participants

Reaction Steps

A solution of 6-(4-tert-butoxycarbonyl-piperazin-1-yl)-2-furan-2-yl-[1,2,4]triazolo[1,5-a]pyrazine-8-carboxylic acid methyl ester (4 mg, 0.009 mmol; see Example 16 (g) above) in 1 N potassium hydroxide methanol solution (1 mL) was stirred at room temperature for 2 hours. The solvent was then removed, and the residue was suspended in water. The resulting suspension was acidified with acetic acid until pH 4 and extracted with methylene chloride three times. The combined organic phases were washed with brine, dried over anhydrous magnesium sulfate, and concentrated to afford 6-(4-tert-butoxycarbonyl-piperazin-1-yl)-2-furan-2-yl-[1,2,4]triazolo[1,5-a]pyrazine-8-carboxylic acid as a yellow solid (2.6 mg, 68%). 1H NMR (300 MHz, CDCl3) δ1.50 (s, 9H), 3.53-3.58 (m, 4H), 3.63-3.68 (m, 4H), 6.63 (dd, J=1.8, 3.3 Hz, 1H), 7.35 (d, J=3.3 Hz, 1H), 7.67 (d, J=1.8 Hz, 1H), 8.08 (s, 1 H); 13C NMR (100 MHz, CDCl3) δ28.39, 45.90, 80.49, 106.62, 112.27, 113.83, 134.92, 142.08, 144.56, 145.30, 149.18, 154.60, 157.09, 161.49.

Provenance & Evidence