1,1-Dimethylhydrazine → 3-(5-Methyl-3-pyridin-2-yl-isoxazol-4-ylmethoxy)-isoxazole-5-carboxylic acid N',N'-dimethyl-hydrazide

HRID 1920913Notes

Reaction equation

HRID 1920913 reaction equation
C[Al](C)C.[CH3:5][N:6]([CH3:8])[NH2:7].C[O:10][C:11]([C:13]1[O:17][N:16]=[C:15]([O:18][CH2:19][C:20]2[C:21]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=3)=[N:22][O:23][C:24]=2[CH3:25])[CH:14]=1)=O.[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>O1CCOCC1>[CH3:5][N:6]([CH3:8])[NH:7][C:11]([C:13]1[O:17][N:16]=[C:15]([O:18][CH2:19][C:20]2[C:21]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=3)=[N:22][O:23][C:24]=2[CH3:25])[CH:14]=1)=[O:10]

Participants

6

Reactant 4

HCID 59761,1-DimethylhydrazineHCID 9357Potassium Sodium TartrateHCID 16682925TrimethylaluminumHCID 674920483-(5-Methyl-3-pyridin-2-yl-isoxazol-4-ylmethoxy)-isoxazole-5-carboxylic acid methyl ester

Product 1

HCID 674922303-(5-Methyl-3-pyridin-2-yl-isoxazol-4-ylmethoxy)-isoxazole-5-carboxylic acid N',N'-dimethyl-hydrazideYield 79%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

A solution of trimethylaluminium (2 M in toluene, 0.6 mL, 1.3 mmol) was added dropwise (exothermic) to a solution of N,N-dimethylhydrazine (76 mg, 1.3 mmol) in dioxane (3 mL) and the resulting mixture was stirred at room temperature for 1 h. Then a solution of 3-(5-methyl-3-pyridin-2-yl-isoxazol-4-ylmethoxy)-isoxazole-5-carboxylic acid methyl ester (100 mg, 0.32 mmol) in dioxane (2 mL) was added. The resulting mixture was then heated at 85-90° C. overnight, cooled to room temperature and poured into Seignette's salt and extracted with ethyl acetate which was then washed with brine, dried over sodium sulfate and evaporated. Purification by chromatography (silica, dichloromethane:methanol=9:1 to 7:3) afforded the title compound (86 mg, 79%) which was obtained as a white solid. MS: m/e=344.2 [M+H]+.

Workup

  1. temperatureThe resulting mixture was then heated at 85-90° C. overnight
  2. temperaturecooled to room temperature
  3. extractionextracted with ethyl acetate which
  4. washwas then washed with brine
  5. dry with materialdried over sodium sulfate
  6. customevaporated
  7. customPurification by chromatography (silica, dichloromethane:methanol=9:1 to 7:3)

Sources & evidence

ORD record
ord-587ff8ab530c4af8920f92ddb2280be7
Source dataset
uspto-grants-2012_05
Patent number
US08173652B2

Reaction notes

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