4-Methylmorpholine → HCID 53496091, compound

Participants

Reaction Steps

(R/S)-2-Hydroxy-2-(4-(5-(5-phenyl-4-(trifluoromethyl)isoxazol-3-yl)-1,2,4-oxadiazol-3-yl)phenyl)acetic acid (Int-IX, 24 mg, 0.049 mmol), ethanamine-HCl (6.01 mg, 0.074 mmol), 4-methylmorpholine (19.88 mg, 0.197 mmol), and HATU (24.29 mg, 0.064 mmol) were added to DMF (1 mL). This was stirred for 1 h before it was purified by prep HPLC (PHENOMENEX® Luna 5u 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 15 min, 20 mL/min, 220 nM, product retention=15.7 min) to provide (R/S)-N-(2-(ethylamino)-2-oxoethyl)-2-hydroxy-2-(4-(5-(5-phenyl-4-(trifluoromethyl)isoxazol-3-yl)-1,2,4-oxadiazol-3-yl)phenyl)acetamide (5 mg, 7.62 μmol, 15.52% yield): LCMS=516.2 [M+H]+; 1H NMR (400 MHz, methanol-d4) δ ppm 8.17 (2 H, d, J=8.36 Hz), 7.59-7.84 (7 H, m), 5.20 (1 H, s), 3.79-3.99 (2 H, m), 3.15-3.27 (2 H, m), 1.11 (3 H, t, J=7.26 Hz); HPLC peak RT=8.6 min (Method A).

Provenance & Evidence