Ammonium Hydroxide → HCID 72463202, compound

Participants

Reaction Steps

To a solution of 3-(3-(1-(5-chloropyridin-2-yl)-1-(3-fluoro-5-(1,1,2,2-tetrafluoroethoxy)phenyl)-2-phenylethyl)ureido)-3-methylbutanoic acid (17.4 mg, 0.03 mmol) in DMF (1 mL) was added HOBt (20 mg, 0.148 mmol) and EDCI (29 mg, 0.151 mmol). The resulting mixture was stirred at room temperature over night, followed by addition of NH4OH (1 mL). After 5 min, the reaction mixture was concentrated and the residue was purified by preparative HPLC Shimadzu-AXIA column, 30×100 mm eluting with 30-100% MeOH (90% in H2O, 0.1% TFA) gradient over 12 min with flow rate 40 mL/min and UV detection at 220 nm to give 3-(3-(1-(5-chloropyridin-2-yl)-1-(3-fluoro-5-(1,1,2,2-tetrafluoroethoxy)phenyl)-2-phenylethyl)ureido)-3-methylbutanamide as a white foam (15.5 mg, 88% yield). LCMS: RT=1.99 min [M+H] 585.3 (LCMS Method 2); NMR: 400 MHz 1H (CDCl3) 8.30 ppm, 1H, d, J=2.0 Hz; 7.75 ppm, 1H, dd, J=8.7, 2.4 Hz; 7.44 ppm, 1H, br. s; 7.16 ppm, 5H, m; 6.99 ppm, 1H, s; 6.92 ppm, 1H, d, J=8.8 Hz; 6.67 ppm, 1H, br. s; 6.57 ppm, 2H, d, J=7.1 Hz; 5.97 ppm, 1H, t, J=53 Hz; 4.10 ppm, 1H, d, J=12.9 Hz; 3.63 ppm, 1H, d, J=13.1 Hz; 2.97 ppm, 1H, d, d=13.1 Hz; 2.44 ppm, 1H, d, J=13.1 Hz; 1.47 ppm, 3H, s; 1.36 ppm, 3H, s.

Provenance & Evidence