Acetonitrile → 2-(3-Bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl)-6-chloro-8-methyl-4H-benzo[d][1,3]oxazin-4-one

HRID 251905

반응식

HRID 251905 반응식
[Br:1][C:2]1[CH:6]=[C:5]([C:7]([OH:9])=O)[N:4]([C:10]2[C:15]([Cl:16])=[CH:14][CH:13]=[CH:12][N:11]=2)[N:3]=1.C(#N)C.CS(Cl)(=O)=O.[NH2:25][C:26]1[C:34]([CH3:35])=[CH:33][C:32]([Cl:36])=[CH:31][C:27]=1[C:28](O)=[O:29]>C(N(CC)CC)C>[Br:1][C:2]1[CH:6]=[C:5]([C:7]2[O:9][C:28](=[O:29])[C:27]3[CH:31]=[C:32]([Cl:36])[CH:33]=[C:34]([CH3:35])[C:26]=3[N:25]=2)[N:4]([C:10]2[C:15]([Cl:16])=[CH:14][CH:13]=[CH:12][N:11]=2)[N:3]=1

참가 물질

6

반응물 4

HCID 6342AcetonitrileHCID 31297Methanesulfonyl chloride2회HCID 115875353-Bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxylic acidHCID 116440442-Amino-5-chloro-3-methylbenzoic acid

생성물 1

HCID 102533072-(3-Bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl)-6-chloro-8-methyl-4H-benzo[d][1,3]oxazin-4-one수율 14.9%

시약·촉매·용매 1

HCID 8471Triethylamine용매2회

실험 절차

To a mixture of 0.44 g of 3-bromo-1-(3-chloro-2-pyridinyl)-1H-pyrazole-5-carboxylic acid, 6 ml of acetonitrile and 0.20 g of triethylamine was added 0.125 ml of methanesulfonyl chloride. After the resulting mixture was stirred at room temperature for 15 minutes, 0.27 g of 2-amino-5-chloro-3-methylbenzoic acid was added and the mixture was stirred at room temperature for 20 minutes. To the mixture, 0.40 ml of triethylamine was added. After the mixture was stirred at room temperature for 20 minutes, 0.13 ml of methanesulfonyl chloride was added and the mixture was stirred at room temperature for 16 hours. The reaction mixture was filtered and the filter cake was washed with methyl tert-butyl ether. The resulting filter cake was dissolved in ethyl acetate, washed successively with water and an aqueous saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to obtain 0.098 g of 2-[3-bromo-1-(3-chloro-2-pyridinyl)-1H-pyrazol-5-yl]-6-chloro-8-methyl-4H-3,1-benzoxazine-4-one. In addition, the filtrate was concentrated under reduced pressure, and the resulting residue was subjected to silica gel column chromatography to obtain 0.093 g of 2-[3-bromo-1-(3-chloro-2-pyridinyl)-1H-pyrazol-5-yl]-6-chloro-8-methyl-4H-3,1-benzoxazine-4-one of the formula:

후처리

  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 16 hours
  4. filtrationThe reaction mixture was filtered
  5. washthe filter cake was washed with methyl tert-butyl ether
  6. filtrationThe resulting filter cake
  7. dissolutionwas dissolved in ethyl acetate
  8. washwashed successively with water
  9. dry with materialan aqueous saturated sodium chloride solution, dried over anhydrous magnesium sulfate
  10. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-780960cf4f784562b8e6dbf60d402b9a
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07867949B2

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