Water → 4-(4-Bromo-2-fluorophenylamino)-6-oxo-1-phenyl-1,6-dihydropyridazine-3-carboxylic acid

HRID 15937

반응식

HRID 15937 반응식
C[O:2][C:3]([C:5]1[C:10](Cl)=[CH:9][C:8](=[O:12])[N:7]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:6]=1)=[O:4].[Br:19][C:20]1[CH:26]=[CH:25][C:23]([NH2:24])=[C:22]([F:27])[CH:21]=1.C(=O)([O-])[O-].[Cs+].[Cs+].O>ClC1C=CC=CC=1Cl.CCOC(C)=O>[Br:19][C:20]1[CH:26]=[CH:25][C:23]([NH:24][C:10]2[C:5]([C:3]([OH:2])=[O:4])=[N:6][N:7]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:8](=[O:12])[CH:9]=2)=[C:22]([F:27])[CH:21]=1

참가 물질

7

반응물 4

HCID 962WaterHCID 10796Cesium carbonateHCID 1230504-Bromo-2-fluoroanilineHCID 2784479Methyl 4-chloro-6-oxo-1-phenyl-1,6-dihydropyridazine-3-carboxylate

생성물 1

HCID 666739604-(4-Bromo-2-fluorophenylamino)-6-oxo-1-phenyl-1,6-dihydropyridazine-3-carboxylic acid수율 43%

시약·촉매·용매 2

HCID 72391,2-Dichlorobenzene용매HCID 8857Ethyl Acetate용매

실험 절차

To a mixture of 4-chloro-6-oxo-1-phenyl-1,6-dihydropyridazine-3-carboxylic acid methyl ester (0.250 g, 0.944 mmol) in 1,2-dichlorobenzene (3.8 mL) was added 4-bromo-2-fluoro aniline (0.561 g, 3.78 mmol), and cesium carbonate (0.615 mg, 1.89 mmol). The reaction mixture was heated to reflux. After 1 hour, the reaction mixture was cooled to room temperature. Water was added and the mixture was diluted with EtOAc. The aqueous layer was separated, acidified with 10% HCl solution, and extracted with EtOAc. The combined organic layers were dried (MgSO4), concentrated under reduced pressure, and triturated to give 0.153 g (43%) of the desired product.

후처리

  1. temperatureThe reaction mixture was heated to reflux
  2. customThe aqueous layer was separated
  3. extractionextracted with EtOAc
  4. dry with materialThe combined organic layers were dried (MgSO4)
  5. concentrationconcentrated under reduced pressure
  6. customtriturated

출처 및 근거

ORD 기록
ord-a2be2e739ec34b94a42de69e3a0075c4
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07732616B2

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