Dimethylformamide → HCID 53495943, 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, 30 mg, 0.070 mmol), pyridin-3-ylmethanamine (11.28 mg, 0.104 mmol), HATU (34.4 mg, 0.090 mmol), and 4-methylmorpholine (28.1 mg, 0.278 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 10 min, 20 mL/min, 220 nM, product retention=10.7 min) to provide (R/S)-2-hydroxy-2-(4-(5-(5-phenyl-4-(trifluoromethyl)isoxazol-3-yl)-1,2,4-oxadiazol-3-yl)phenyl)-N-(pyridin-3-ylmethyl)acetamide-TFA (20 mg, 0.029 mmol, 41.8% yield): LCMS=522.2 [M+H]+; 1H NMR (400 MHz, methanol-d4) δ ppm 8.72 (2 H, br. s.), 8.47 (1 H, d, J=8.14 Hz), 8.15 (2 H, d, J=8.58 Hz), 7.99 (1 H, dd, J=7.92, 5.94 Hz), 7.57-7.88 (7 H, m), 5.22 (1 H, s), 4.62 (2 H, s); HPLC peak RT=7.7 min (Method A).

Provenance & Evidence