Ethanolamine → HCID 67172602, 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)propanoic acid (Preparation 134D, isomer 2, 15 mg, 0.032 mmol) in DMF (1 mL) was added 2-aminoethanol (2.9 mg, 0.048 mmol), 4-methylmorpholine (12.9 mg, 0.13 mmol) and BOP (18.3 mg, 0.041 mmol). The reaction mixture was stirred for 1 h. Methanol was added and it was purified by prep HPLC (Phenomenex Luna 5 u 21.2×100 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 10 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)propanamide (5 mg, 9.52 μmol, 29.9% yield) as a white solid: product HPLC ret. time=9.15 min. (condition G); LC/MS M+1=514.06; 1H NMR (400 MHz, CD3OD) δ ppm 8.09-8.20 (1H, m), 7.91 (1H, d, J=7.92 Hz), 7.77 (2H, d, J=7.48 Hz), 7.51-7.72 (5H, m), 3.60 (2H, td, J=5.72, 3.08 Hz), 3.36-3.40 (2H, m), 3.07 (4H, s), 1.78 (3H, s).

Provenance & Evidence