Methanol → 1-{4-[7-(4-Methanesulfonyl-phenyl)-imidazo[1,2-a]pyridin-3-yl]-benzyl}-3-(3-trifluoromethyl-phenyl)-urea

Dissolve 4-[7-(4-methanesulfonyl-phenyl)-imidazo[1,2-a]pyridin-3-yl]-benzylamine (2.37 g, 6.28 mmol) and diisopropylethylamine (2.44 g, 3.28 mL, 18.84 mmol) in dimethylsulfoxide under a nitrogen environment at room temperature. Add 3-trifluoromethylphenylisocyanate (1.17 g, 6.28 mmol) and stir the mixture for 2.5 hours. Pour the reaction contents onto a Varian SCX column (50 g) prewashed with methanol. Wash the column with dichloromethane, 1:1 methanol/dichloromethane and methanol (150 mL each). Elute the title compound with 2 N NH3/methanol (300 mL). Concentrate the methanolic solution to dryness and chromatograph on silica using 0→3→5→10% methanol/dichloromethane over 4, 15 and 30 minutes, respectively. Dissolve the product in heated CHCl3 (65 mL), followed by treatment with hexanes (5 mL) and cooling. Dry the resulting precipitate in vacuo to yield the product (2.33 g, 66%). MS(ES), m/z 565 (M+1).

1. additionPour
2. customthe reaction contents onto a Varian SCX column (50 g)
3. washWash the column with dichloromethane, 1:1 methanol/dichloromethane and methanol (150 mL each)
4. washElute the title compound with 2 N NH3/methanol (300 mL)
5. concentrationConcentrate the methanolic solution to dryness and chromatograph on silica using 0→3→5→10% methanol/dichloromethane over 4, 15 and 30 minutes
6. dissolutionDissolve the product in heated CHCl3 (65 mL)
7. temperaturecooling
8. customDry the resulting precipitate in vacuo

ORD 기록

ord-8dd589494a32418aabdd969f6e7aecaf

출처 데이터셋

uspto-grants-2010_02

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US07666879B2