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Methylhydrazine → 3-Bromo-n-[4,6-dibromo-2-(n-methylhydrazinocarbonyl)phenyl]-1-(3-chloro-2-pyridinyl)-1h-pyrazole-5-carboxamide

HRID 2427112
Notes
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Reaction equation

HRID 2427112 reaction equation
[Br:1][C:2]1[CH:6]=[C:5]([C:7]2[O:12][C:11](=[O:13])[C:10]3[CH:14]=[C:15]([Br:19])[CH:16]=[C:17]([Br:18])[C:9]=3[N:8]=2)[N:4]([C:20]2[C:25]([Cl:26])=[CH:24][CH:23]=[CH:22][N:21]=2)[N:3]=1.[CH3:27][NH:28][NH2:29].O1CCCC1>O>[Br:1][C:2]1[CH:6]=[C:5]([C:7]([NH:8][C:9]2[C:17]([Br:18])=[CH:16][C:15]([Br:19])=[CH:14][C:10]=2[C:11]([N:28]([CH3:27])[NH2:29])=[O:13])=[O:12])[N:4]([C:20]2[C:25]([Cl:26])=[CH:24][CH:23]=[CH:22][N:21]=2)[N:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6061MethylhydrazineHCID 8028TetrahydrofuranHCID 592003072-[5-bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazol-3-yl]-6,8-dibromo-benzo[d][1,3]oxazin-4-one

Product 1

HCID 668543613-Bromo-n-[4,6-dibromo-2-(n-methylhydrazinocarbonyl)phenyl]-1-(3-chloro-2-pyridinyl)-1h-pyrazole-5-carboxamide

Reagents, catalysts & solvents 1

HCID 962
Water
Solvent

Procedure

A mixture of 1.0 g of 2-[3-bromo-1-(3-chloro-2-pyridinyl)-1H-pyrazol-5-yl]-6,8-dibromo-4H-3,1-benzoxazine-4-one, 0.28 ml of methylhydrazine and 16 ml of tetrahydrofuran 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 0.97 g of 3-bromo-N-[4,6-dibromo-2-(N-methylhydrazinocarbonyl)phenyl]-1-(3-chloro-2-pyridinyl)-1H-pyrazole-5-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-1363b424c87b4b3fa7a8037176632641
Source dataset
uspto-grants-2011_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07968573B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes