1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 54579915, compound

Participants

Reaction Steps

5,5,5-Trifluoropentanoic acid (1.3 equiv), EDCI (1.3 equiv), HOBt (0.3 equiv) and DIEA (4 equiv) were mixed in DMF (40 mL) for 5 minutes. 4-(3-thiazol-2-yl-[1,2,4]oxadiazol-5-yl)-piperidine hydrochloride (5c) (8.18 g, 30 mmol, 1 equiv) was added with 20 mL of DMF and the reaction mixture was stirred overnight at room temperature and then evaporated under reduced pressure. The residue was dissolved in AcOEt and then washed twice with saturated aqueous NaHCO3, twice with HCl 1N and once with brine, then dried over MgSO4 and evaporated under reduced pressure. The residue was purified by chromatography on silica gel (DCM/MeOH 100-0 to 98.5-1.5) and then recrystallized in a mixture of isopropanol and diisopropyl ether. Yield 62%; 1H NMR (CD2Cl2) δ 8.06 (d, J=3.0 Hz, 1H), 7.65 (d, J=3.0 Hz, 1H), 4.51-4.55 (m, 1H), 3.90-3.95 (m, 1H), 3.22-3.39 (m, 2H), 2.91-2.98 (m, 1H), 2.44 (t, J=7.2 Hz, 2H), 2.15-2.27 (m, 4H), 1.83-2.01 (m, 4H); 13C NMR (CDCl3) δ 182.06, 169.56, 163.97, 154.00, 144.95, 127.37 (q, J=275 Hz), 122.66, 44.33, 40.60, 34.43, 32.97 (q, J=29 Hz), 31.34, 29.44, 28.90, 17.52. mp 75.6-76.3° C.; tR LCMS 6.1 min. Purity >99%; MS [M+H]+ m/z 375.

Provenance & Evidence