Ethanolamine → HCID 67171544, compound

Participants

Reaction Steps

To 2-hydroxy-2-(3-(5-phenyl-4-(trifluoromethyl)isoxazol-3-yl)-4,5-dihydronaphtho[1,2-c]isoxazol-7-yl)acetic acid (Preparation 131B, isomer 1, 40 mg, 0.088 mmol) in DMF (1 mL) was added 2-aminoethanol (8.03 mg, 0.131 mmol), BOP (46.5 mg, 0.105 mmol), and 4-methylmorpholine (53.2 mg, 0.526 mmol). The reaction mixture was stirred for 1 h. Methanol was added and it was purified by prep HPLC (Phenomenex 21.2×250 mm, Solvent A: 90% water with 10% acetonitrile and 0.1% TFA, Solvent B: 90% acetonitrile with 10% water and 0.1% TFA, Gradient: 0% B to 100% B over 30 min, 20 mL/min, 220 nM) to yield 2-hydroxy-N-(2-hydroxyethyl)-2-(3-(5-phenyl-4-(trifluoromethyl)isoxazol-3-yl)-4,5-dihydronaphtho[1,2-c]isoxazol-7-yl)acetamide (23 mg, 0.045 mmol, 51.5% yield) as a white solid: product HPLC ret. time=8.83 min (condition G); LC/MS M+1=500.04; 1H NMR (400 MHz, DMSO-d6) δ ppm 7.96 (1H, t, J=5.83 Hz), 7.87 (1H, d, J=7.92 Hz), 7.80 (2H, d, J=7.26 Hz), 7.63-7.75 (3H, m), 7.45-7.52 (2H, m), 6.34 (1H, d, J=4.84 Hz), 4.99 (1H, d, J=4.62 Hz), 4.71 (1H, t, J=5.28 Hz), 3.43 (2H, q, J=5.94 Hz), 3.12-3.24 (2H, m), 3.04 (4H, s).

Provenance & Evidence