Trifluoroacetic acid → HCID 58451281, 화합물

반응식

[CH:1]1([C:4]([NH:6][C:7]2[S:8][C:9]3[C:14]([N:15]=2)=[CH:13][CH:12]=[C:11]([O:16][C:17]2[CH:18]=[C:19]([NH:24]C(=O)OC(C)(C)C)[CH:20]=[CH:21][C:22]=2[CH3:23])[N:10]=3)=[O:5])[CH2:3][CH2:2]1.C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O>>[NH2:24][C:19]1[CH:20]=[CH:21][C:22]([CH3:23])=[C:17]([CH:18]=1)[O:16][C:11]1[N:10]=[C:9]2[S:8][C:7]([NH:6][C:4]([CH:1]3[CH2:3][CH2:2]3)=[O:5])=[N:15][C:14]2=[CH:13][CH:12]=1

참가 물질

반응물 3

HCID 6422Trifluoroacetic acid

HCID 7519Anisole

HCID 59507073Tert-butyl [3-({2-[(cyclopropylcarbonyl)amino][1,3]thiazolo[5,4-b]pyridin-5-yl}oxy)-4-methylphenyl]carbamate

생성물 1

HCID 58451281HCID 58451281, 화합물수율 85%

실험 절차

To tert-butyl [3-({2-[(cyclopropylcarbonyl)amino][1,3]thiazolo[5,4-b]pyridin-5-yl}oxy)-4-methylphenyl]carbamate (0.80 g, 1.82 mmol) produced in Example C46(v) were added anisole (0.5 mL) and trifluoroacetic acid (5.0 mL) at 4° C. to give a solution, and the solution was stirred at the same temperature for 2 hr. The reaction mixture was concentrated under reduced pressure, saturated aqueous sodium hydrogen carbonate solution (80 mL) was added to the obtained oily residue, and the mixture was extracted with ethyl acetate (80 mL)/tetrahydrofuran (8 mL). The organic layer was washed with saturated brine (80 mL), and dried over anhydrous sodium sulfate. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by basic silica gel column chromatography (ethyl acetate), and the obtained solution was concentrated under reduced pressure. The residue was triturated with hexane to give the title compound (525 mg, 85%) as a colorless powder.