Triethylamine → 8-chloro-2-[1-(3-chloro-2-pyridinyl)-3-trifluoromethyl-1H-pyrazol-5-yl]-4H-3,1-benzoxazine-4-one

To a solution of 0.80 g of 1-(3-chloro-2-pyridinyl)-3-trifluoromethyl-1H-pyrazole-5-carbonyl chloride in 20 ml of acetonitrile, 0.44 g of 2-amino-3-chlorobenzoic acid was added. The mixture was stirred at room temperature for 10 minutes and then, 0.36 ml of triethylamine was added thereto. The mixture was stirred at room temperature for 20 minutes and then, 0.72 ml of triethylamine was further added thereto. After the mixture was stirred at room temperature for 20 minutes, 0.22 ml of methanesulfonyl chloride was added and the mixture was stirred at room temperature for 20 hours. Water was poured into the reaction mixture, and the mixture was extracted with ethyl acetate two times. The organic layers were combined, washed with an aqueous saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to obtain 1.17 g of 8-chloro-2-[1-(3-chloro-2-pyridinyl)-3-trifluoromethyl-1H-pyrazol-5-yl]-4H-3,1-benzoxazine-4-one of the formula:

1. stirringThe mixture was stirred at room temperature for 20 minutes
2. stirringAfter the mixture was stirred at room temperature for 20 minutes
3. stirringthe mixture was stirred at room temperature for 20 hours
4. extractionthe mixture was extracted with ethyl acetate two times
5. washwashed with an aqueous saturated sodium chloride solution
6. dry with materialdried over anhydrous magnesium sulfate
7. concentrationconcentrated under reduced pressure

ORD 기록

ord-d542499982454e92ac95b03df2e271f8

출처 데이터셋

uspto-grants-2011_01

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US07867949B2