4-Methylmorpholine → HCID 53496991, compound

Participants

Reaction Steps

(R/S)-2-Hydroxy-2-(4-(5-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-1,2,4-oxadiazol-3-yl)phenyl)acetic acid (Int-V, 20 mg, 0.046 mmol) was dissolved in DMF (1 mL) prior to the addition of 4-methylmorpholine (0.031 mL, 0.278 mmol), N-methylethanamine (4.93 mg, 0.083 mmol), and HATU (31.7 mg, 0.083 mmol). This was stirred overnight and was then purified by preparative HPLC (PHENOMENEX® Luna 5u C18 21.2×100 mm, gradient elution with Method 1—MeOH/water containing 0.1% trifluoroacetic acid as defined above, 0% B to 100% B over 10 min, 20 mL/min, 220 nM, product retention=12.2 min) to give (R/S)-N-ethyl-2-hydroxy-N-methyl-2-(4-(5-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-1,2,4-oxadiazol-3-yl)phenyl)acetamide (11 mg, 0.022 mmol, 47.7% yield): LCMS=473.2 [M+H]+; 1H NMR (mixture of rotamers, 400 MHz, methanol-d4) δ ppm 8.16-8.27 (2H, m), 7.48-7.75 (7 H, m), 5.54 (1 H, s), 5.51 (1 H, s), 3.35-3.55 (2 H, m), 2.96 (3 H, s), 2.91 (3 H, s), 1.11 (3 H, t, J=7.15 Hz), 0.92 (3 H, t, J=7.04 Hz).

Provenance & Evidence