Diisopropylethylamine → 5-(3-Chloro-phenyl)-3-(2-furan-2-yl-3-methyl-3H-imidazol-4-ylsulfanylmethyl)-[1,2,4]oxadiazole

2-Furan-2-yl-3-methyl-3,5-dihydro-imidazol-4-one (described in Takeuchi, H., Hagiwara, S., Eguchi, S., Tetrahedron (1989) 6375-6386) (50 mg, 0.30 mmol) was dissolved in dioxane (3 ml) and Lawesson reagent (136 mg, 0.34 mmol) was added. The reaction mixture was heated to reflux over night and then allowed to room temperature at which time DIPEA (212 ml, 1.22 mmol) and 3-chloromethyl-5-(3-chloro-phenyl)-[1,2,4]oxadiazole (140 mg, 0.61 mmol) was added. The resulting mixture was heated to reflux for 5 h and then kept at room temperature over night. Ethyl acetate was added and the reaction mixture was washed with water followed by brine. The organic phase was dried over MgSO4 and evaporated. The title compound (13 mg, 11%) was obtained by flash chromatography using 1% methanol in chloroform. 1H NMR (CD3OD) d (ppm): 7.96 (m, 1H), 7.90 (m, 1H), 7.60 (dd, 1H), 7.57 (ddd, 1H), 7.46 (t, 1H), 7.09 (s, 1H), 6.86 (dd, 1H), 6.52 (dd, 1H), 3.95 (s, 2H), 3.74 (s, 3H).

1. temperatureThe reaction mixture was heated
2. temperatureto reflux over night
3. additionwas added
4. temperatureThe resulting mixture was heated
5. temperatureto reflux for 5 h
6. waitkept at room temperature over night
7. washthe reaction mixture was washed with water
8. dry with materialThe organic phase was dried over MgSO4
9. customevaporated

ORD record

ord-1ec41ffe69c34a9f875d2bfcada96b07

Source dataset

uspto-grants-2008_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07456200B2