Water → HCID 59355290, compound

HRID 887717Notes

Reaction equation

HRID 887717 reaction equation
Cl.Cl.[CH3:3][NH:4][NH:5][CH3:6].C(=O)([O-])[O-].[K+].[K+].[Br:13][C:14]1[CH:15]=[C:16]([C:26]2[O:27][C:28](=[O:38])[C:29]3[N:35]=[C:34]([Cl:36])[CH:33]=[C:32]([CH3:37])[C:30]=3[N:31]=2)[N:17]([C:19]2[C:24]([Cl:25])=[CH:23][CH:22]=[CH:21][N:20]=2)[N:18]=1.O>C1COCC1.O.C(OCC)(=O)C>[Cl:36][C:34]1[N:35]=[C:29]([C:28]([N:4]([CH3:3])[NH:5][CH3:6])=[O:38])[C:30]([NH:31][C:26]([C:16]2[N:17]([C:19]3[C:24]([Cl:25])=[CH:23][CH:22]=[CH:21][N:20]=3)[N:18]=[C:14]([Br:13])[CH:15]=2)=[O:27])=[C:32]([CH3:37])[CH:33]=1

Participants

8

Reactant 4

HCID 962WaterHCID 93801,2-Dimethylhydrazine dihydrochlorideHCID 11430Potassium CarbonateHCID 59355358HCID 59355358, compound

Product 1

HCID 59355290HCID 59355290, compoundYield 88.3%

Reagents, catalysts & solvents 3

HCID 962WaterCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

1,2-Dimethylhydrazine dihydrochloride (176 mg) and potassium carbonate (366 mg) were suspended in THF (8 mL) and 10 drops of water, 2-[5-bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazol-3-yl]-6-chloro-8-methyl-pyrido[3,2-d][1,3]oxazin-4-one (example 7, step 4) (300 mg) was added and the reaction mixture was stirred for 20 h at room temperature. Water and ethyl acetate were added, the layers were separated and the aqueous layer was 2× extracted with ethyl acetate. The combined organic layer was washed with brine, dried over magnesium sulfate and concentrated in vacuum. The residue was purified by column chromatography (silica 60, chloroform/ethyl acetate=1:1, Rf=0.13) to afford 300 mg of the title compound of the formula

Workup

  1. customthe layers were separated
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuum
  6. customThe residue was purified by column chromatography (silica 60, chloroform/ethyl acetate=1:1, Rf=0.13)

Sources & evidence

ORD record
ord-13b350d5558047c3a1a785187e60fe31
Source dataset
uspto-grants-2012_08
Patent number
US08247431B2

Reaction notes

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