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

HRID 252004

Reaction equation

HRID 252004 reaction equation
Cl.Cl.[CH3:3][NH:4][NH:5][CH3:6].C(=O)([O-])[O-].[K+].[K+].O1CCCC1.[Br:18][C:19]1[CH:20]=[C:21]([Br:43])[C:22]2[N:27]=[C:26]([C:28]3[N:29]([C:34]4[C:39]([Cl:40])=[CH:38][CH:37]=[CH:36][N:35]=4)[CH:30]=[C:31]([Br:33])[CH:32]=3)[O:25][C:24](=[O:41])[C:23]=2[CH:42]=1>O>[Br:33][C:31]1[CH:32]=[C:28]([C:26]([NH:27][C:22]2[C:21]([Br:43])=[CH:20][C:19]([Br:18])=[CH:42][C:23]=2[C:24]([N:4]([CH3:3])[NH:5][CH3:6])=[O:41])=[O:25])[N:29]([C:34]2[C:39]([Cl:40])=[CH:38][CH:37]=[CH:36][N:35]=2)[CH:30]=1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 93801,2-Dimethylhydrazine dihydrochlorideHCID 11430Potassium CarbonateHCID 668541976,8-dibromo-2-[4-bromo-1-(3-chloro-2-pyridinyl)-1H-pyrrol-2-yl]-4H-3,1-benzoxazine-4-one

Product 1

HCID 577803304-bromo-N-[4,6-dibromo-2-(N,N'-dimethylhydrazinocarbonyl)phenyl]-1-(3-chloro-2-pyridinyl)-1H-pyrrole-2-carboxamideYield 79.6%

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 962WaterSolvent

Procedure

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 0.59 g of 6,8-dibromo-2-[4-bromo-1-(3-chloro-2-pyridinyl)-1H-pyrrol-2-yl]-4H-3,1-benzoxazine-4-one. The resulting mixture was stirred at room temperature for 2 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 0.52 g of 4-bromo-N-[4,6-dibromo-2-(N,N′-dimethylhydrazinocarbonyl)phenyl]-1-(3-chloro-2-pyridinyl)-1H-pyrrole-2-carboxamide of the formula:

Workup

  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

Sources & evidence

ORD record
ord-bda843301c224fc7b8683dd5bb097550
Source dataset
uspto-grants-2011_01
Patent number
US07867949B2

Linked notes

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