반응 #67034

반응 방정식

methyl 2-(4-carbamoyl-3-fluorophenylamino)-2-methylpropanoate

2-(trifluoromethyl)-4-isothiocyanatobenzonitrile

→

4-(3-(4-cyano-3-(trifluoromethyl)phenyl)-5,5-dimethyl-4-oxo-2-thioxoimidazolidin-1-yl)-2-fluorobenzamide

용매

water

DMSO

반응 조건

후처리

1. 1
   추출extracted with ethyl acetate
2. 2
   농축The combined organic layer was concentrated under reduced pressure
3. 3
   기타the residue was purified by silica gel chromatography
4. 4
   세척eluting with 40% Acetone-Hexanes
5. 5
   workup.WAIT10% to 90% B in 3 min
6. 6
   workup.WAIThold for 3 min
7. 7
   workup.WAIT90% to 10% B in 5 min
8. 8
   기타Retention time, 2.782 min, HPLC Purity, 99.4%, Flow Rate, 1 mL/min

실험 절차

A solution of methyl 2-(4-carbamoyl-3-fluorophenylamino)-2-methylpropanoate and 2-(trifluoromethyl)-4-isothiocyanatobenzonitrile (1.5 equivalents) in dry DMSO (5 mL per mmol) was heated to 80-82° C. for 12 h. The reaction mixture was diluted with water and extracted with ethyl acetate. The combined organic layer was concentrated under reduced pressure and the residue was purified by silica gel chromatography eluting with 40% Acetone-Hexanes. MS (m/z): 451 (M+1). HPLC: Column, YMC ODS A, 4.6×150 mm, 5 μm, Mobile Phase A:10 mM Ammonium acetate, Mobile Phase B: Acetonitrile, Gradient, 10% B up to 2 min, 10% to 90% B in 3 min, hold for 3 min, 90% to 10% B in 5 min, Retention time, 2.782 min, HPLC Purity, 99.4%, Flow Rate, 1 mL/min. 1H NMR (CDCl3, Freebase): δ (ppm) 8.3 (t, 1H), 8.0 (d, 1H) 7.98 (s, 1H), 7.8 (d, 1H), 7.27 (d, 1H), 7.2 (d, 1H), 6.65 (d, 1H), 6.0 (s, 1H), 1.62 (s,6H).

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