4-Methylmorpholine → HCID 53496728, 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, 0.061 mmol) was dissolved in DMF (1 mL) prior to the addition of 4-methylmorpholine (0.041 mL, 0.369 mmol), ethanamine, HCl (9.02 mg, 0.111 mmol), and HATU (42.0 mg, 0.111 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=11.6 min) to give (R/S)-N-(2-(ethylamino)-2-oxoethyl)-2-hydroxy-2-(4-(5-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-1,2,4-oxadiazol-3-yl)phenyl)acetamide (8.6 mg, 0.014 mmol, 23.60% yield): LCMS=516.2[M+H]+; 1H NMR (400 MHz, methanol-d4) δ ppm 8.18 (2 H, d, J=8.36 Hz), 7.65-7.78 (4 H, m), 7.53-7.65 (3 H, m), 5.20 (1 H, s), 3.81-3.96 (2 H, m), 3.23 (2 H, q, J=7.26 Hz), 1.07-1.14 (3 H, m). HPLC Peak RT=9.5 min (Analytical Method D).

Provenance & Evidence