Phosgene → HCID 58997079, compound

Participants

Reaction Conditions

Reaction Steps

To a 0° C. solution of COMPOUND 249 (144 mg, 0.465 mmol) in toluene (20 mL) and Et3N (0.40 mL, 3.34 mmol) was added phosgene solution in toluene (20 wt %, 0.317 mL, 0.697 mmol). The mixture was stirred at 0° C. for 3 hours, was then warmed up to room temperature and solvent was removed under reduced pressure (high vac.) to yield a yellow solid. The solid was dissolved in CH2Cl2 (15 mL) and Et3N (0.194 mL, 1.40 mmol) was added followed by NH2OH.HCl (48 mg, 0.700 mmol). The mixture was stirred at room temperature for 17 hours. Solvent was removed under reduced pressure and the residue was purified by radial chromatography on silica gel (9:1:0.2 CH2Cl2:MeOH:NH4OH) to provide COMPOUND 324 as white solid (112 mg, 60%). 1H NMR (CDCl3) δ 1.61-1.73 (m, 3H), 1.92-2.00 (m, 2H), 2.08 (s, 6H), 2.65-2.72 (m, 3H), 3.81 (s, 4H), 4.01-4.06 (m, 2H), 6.72 (br s, 1H), 7.09 (dd, 2H, J=4.8, 7.8 Hz), 7.37 (d, 2H, J=7.8 Hz), 8.34 (d, 2H, J=4.8 Hz); 13C NMR (CDCl3) δ 18.0, 26.9, 43.8, 54.6, 57.3, 122.5, 133.4, 138.1, 145.9, 157.0, 160.7; ES-MS m/z 370 (M+H). Anal. Calcd. for C20H27N5O2.0.4 CH2Cl2: C, 60.73; H, 6.95; N, 17.36. Found: C, 61.07; H, 7.19; N, 17.09.

Provenance & Evidence