Tetrahydrofuran → 3-bromo-N-[4,6-dibromo-2-(N,N'-dimethylhydrazinocarbonyl)phenyl]-1-(3-chloro-2-pyridinyl)-1H-pyrazole-5-carboxamide

HRID 2427113

Reaktionsgleichung

Reaktionsgleichung von HRID 2427113
Cl.Cl.[CH3:3][NH:4][NH:5][CH3:6].C(=O)([O-])[O-].[K+].[K+].O1CCCC1.[Br:18][C:19]1[CH:23]=[C:22]([C:24]2[O:29][C:28](=[O:30])[C:27]3[CH:31]=[C:32]([Br:36])[CH:33]=[C:34]([Br:35])[C:26]=3[N:25]=2)[N:21]([C:37]2[C:42]([Cl:43])=[CH:41][CH:40]=[CH:39][N:38]=2)[N:20]=1>O>[Br:18][C:19]1[CH:23]=[C:22]([C:24]([NH:25][C:26]2[C:34]([Br:35])=[CH:33][C:32]([Br:36])=[CH:31][C:27]=2[C:28]([N:4]([CH3:3])[NH:5][CH3:6])=[O:30])=[O:29])[N:21]([C:37]2[C:42]([Cl:43])=[CH:41][CH:40]=[CH:39][N:38]=2)[N:20]=1

Komponenten

7

Edukt 4

HCID 8028TetrahydrofuranHCID 93801,2-Dimethylhydrazine dihydrochlorideHCID 11430Potassium CarbonateHCID 592003072-[5-bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazol-3-yl]-6,8-dibromo-benzo[d][1,3]oxazin-4-one

Produkt 1

HCID 577803813-bromo-N-[4,6-dibromo-2-(N,N'-dimethylhydrazinocarbonyl)phenyl]-1-(3-chloro-2-pyridinyl)-1H-pyrazole-5-carboxamideAusbeute 76,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterKatalysatorHCID 962WaterLösungsmittel

Versuchsvorschrift

To a mixture of 0.42 g of N,N′-dimethylhydrazine dihydrochloride, five drops of water, 0.87 g of potassium carbonate and 10 ml of tetrahydrofuran was added 0.60 g of 2-[3-bromo-1-(3-chloro-2-pyridinyl)-1H-pyrazol-5-yl]-6,8-dibromo-4H-3,1-benzoxazine-4-one. The resulting mixture was stirred at room temperature for 19 hours. Water was poured into the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed successively with water and an aqueous saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel chromatography to obtain 0.51 g of 3-bromo-N-[4,6-dibromo-2-(N,N′-dimethylhydrazinocarbonyl)phenyl]-1-(3-chloro-2-pyridinyl)-1H-pyrazole-5-carboxamide of the formula:

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed successively with water
  3. dry with materialan aqueous saturated sodium chloride solution, dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-d5945a96419c4a52af0ae8faff9b51f2
Quelldatensatz
uspto-grants-2011_06
Patentnummer
US07968573B2

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