Triethylamine → HCID 16041744, compound

Participants

Reaction Steps

The compound of Example 5 (1.35 g) was dissolved in 15 mL of THF; and 0.505 mL of NEt3 and 669 mg of 4-nitrophenyl chloroformate were added thereto in order, and stirred at room temperature. The reaction mixture was filtered, and 0.226 mL of 25% aqueous ammonia was added to the filtrate, and stirred overnight at room temperature. The reaction solution was diluted with chloroform, washed with water, dried over magnesium sulfate, and concentrated. The residue was purified through silica gel thin-layer chromatography (CHCl3/MeOH=7/1) to obtain the intended compound as a yellow amorphous solid. 1H-NMR (400 MHz, DMSO-d6) δ: 8.59 (1H, s), 7.80 (1H, d, J=2.9 Hz), 7.66 (1H, dd, J=8.5, 1.5 Hz), 7.53 (1H, dd, J=8.6, 3.0 Hz), 7.50 (1H, t, J=8.4 Hz), 7.22 (1H, dd, J=8.0, 2.0 Hz), 7.16 (1H, s), 6.99 (1H, d, J=8.8 Hz), 5.83 (2H, s), 4.21-4.36 (1H, m), 4.05 (3H, s), 3.93 (3H, s), 3.64-3.55 (1H, m), 3.46-3.32 (1H, m), 3.31-3.20 (1H, m), 2.84 (2H, s), 2.08-1.99 (1H, m), 1.91-1.84 (1H, m), 1.83-1.70 (2H, m). MS [M+H]+=491.

Provenance & Evidence