4-Methylmorpholine → HCID 53496732, 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, 30 mg, 0.070 mmol) was dissolved in DMF (1 mL) prior to the addition of 4-methylmorpholine (0.061 mL, 0.556 mmol), methanamine-HCl (4.70 mg, 0.070 mmol), and HATU (39.7 mg, 0.104 mmol). The reaction mixture was stirred overnight and 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 time=11.7 min) to give (R/S)-2-hydroxy-N-methyl-2-(4-(5-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-1,2,4-oxadiazol-3-yl)phenyl)acetamide (7 mg, 0.014 mmol, 20.3% yield): LCMS=445.1 [M+H]+); 1H NMR (400 MHz, methanol-d4) δ ppm 8.17 (2 H, d, J=7.92 Hz), 7.65-7.78(4 H, m), 7.49-7.66 (3 H, m), 5.12 (1 H, s), 2.79(3 H, s); HPLC Peak RT=8.3 min (Analytical Method A).

Provenance & Evidence