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 2, 25 mg, 0.055 mmol) in DMF (1 mL) was added 2-aminoethanol (5.02 mg, 0.082 mmol), BOP (31.5 mg, 0.071 mmol), and 4-methylmorpholine (33.2 mg, 0.329 mmol). The reaction mixture was stirred for 30 min. Methanol was added and it was purified by prep HPLC (Phenomenex 21.2×250 mm, Solvent A: 90% water with 10% MeOH and 0.1% TFA, Solvent B: 90% MeOH 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 (18 mg, 0.036 mmol, 65.3% yield) as a white solid: product HPLC ret. time=8.66 min (condition G); LC/MS M+1=500.04; 1H NMR (400 MHz, DMSO-d6) δ ppm 7.96 (1H, t, J=5.72 Hz), 7.87 (1H, d, J=7.92 Hz), 7.80 (2H, d, J=7.26 Hz), 7.63-7.76 (3H, m), 7.44-7.53 (2H, m), 6.34 (1H, d, J=4.84 Hz), 4.98 (1H, d, J=4.62 Hz), 4.71 (1H, t, J=5.50 Hz), 3.43 (2H, q, J=5.94 Hz), 3.11-3.24 (2H, m), 3.04 (4H, s).

Provenance & Evidence