Ethyl 2-(morpholin-3-yl)acetate → HCID 50923567, compound

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Reaction Conditions

Reaction Steps

To a mixture of 3-(4-(oxiran-2-yl)phenyl)-5-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-1,2,4-oxadiazole, Preparation 28C (30 mg, 0.075 mmol) in ethanol (2 mL) was added ethyl 2-(morpholin-3-yl)acetate (52.1 mg, 0.301 mmol). The resulting mixture was heated at 80° C. overnight. Solvent was removed in vacuo. The residue was treated with 6N HCl/MeCN at 50° C. overnight. The reaction mixture was filtered and purified by HPLC. HPLC conditions: PHENOMENEX® Luna C18 5 micron column (250×30 mm); 25-100% CH3CN/water (0.1% TFA); 25 minute gradient; 30 mL/min. Isolated fractions with correct mass were freeze-dried overnight to yield 18 mg of 2-(4-(2-hydroxy-2-(4-(5-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)morpholin-3-yl)acetic acid as a TFA salt. 1H NMR (400 MHz, MeOH-d3) δ ppm 8.23 (2H, d, J=7.91 Hz), 7.72 (2H, dd, J=8.35, 2.20 Hz), 7.68 (2H, d, J=7.03 Hz), 7.53-7.65 (3H, m), 5.22-5.30 (1H, m), 3.61-4.21 (7H, m), 3.35-3.55 (2H, m), 2.88-3.10 (2H, m). MS (m+1)=545. HPLC Peak RT=3.23 minutes (Analytical Method A). Purity=93%.

Provenance & Evidence