Dimethylformamide → HCID 53496737, compound

Participants

Reaction Steps

2-Hydroxy-2-(4-(5-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-1,2,4-oxadiazol-3-yl)phenyl)acetic acid (Int-Va, 20 mg, 0.046 mmol), (R/S)-2-phenylglycinonitrile hydrochloride (11.73 mg, 0.070 mmol), 4-methylmorpholine (18.76 mg, 0.185 mmol), and HATU (22.92 mg, 0.060 mmol) were added to DMF (2 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 10 min, product retention=12.2 min (20 mL/min, 220 nM) to provide N-(cyano(phenyl)methyl)-2-hydroxy-2-(4-(5-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-1,2,4-oxadiazol-3-yl)phenyl)acetamide (8 mg, 0.013 mmol, 27.2% yield) as a mixture of diastereomers. LCMS=546.3 [M+H]+; 1H NMR (400 MHz, methanol-d4) δ ppm 8.17 (2 H, dd, J=8.36, 6.38 Hz), 7.32-7.77 (12 H, m), 6.18 (1 H, d, J=7.04 Hz), 5.24 (1 H, d, J=8.14 Hz); HPLC peak RT=10.9 min (Method A).

Provenance & Evidence