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Isopropylamine → 3-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-isoxazole-5-carboxylic acid isopropylamide

HRID 1920899
Notes
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Reaction equation

HRID 1920899 reaction equation
C[Al](C)C.[CH:5]([NH2:8])([CH3:7])[CH3:6].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][CH: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>[CH:5]([NH:8][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][CH:27]=3)=[N:22][O:23][C:24]=2[CH3:25])[CH:14]=1)=[O:10])([CH3:7])[CH3:6]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6363IsopropylamineHCID 9357Potassium Sodium TartrateHCID 16682925TrimethylaluminumHCID 674922963-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-isoxazole-5-carboxylic acid methyl ester

Product 1

HCID 468968863-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-isoxazole-5-carboxylic acid isopropylamideYield 74%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of trimethylaluminium (2 M in toluene, 1.27 mL, 2.6 mmol) was added dropwise (exothermic) to a solution of isopropyl amine (220 μL, 2.6 mmol) in dioxane (6 mL) and the resulting mixture was stirred at room temperature for 30 min. Then 3-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-isoxazole-5-carboxylic acid methyl ester (230 mg, 0.73 mmol) was added. The resulting mixture was then heated at 85-90° C. for 30 min and then cooled to room temperature and then 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, heptane:ethyl acetate=4:1 to 0:1) afforded the title compound (184 mg, 74%) which was obtained as a white solid. MS: m/e=342.1 [M+H]+.

Workup

  1. temperatureThe resulting mixture was then heated at 85-90° C. for 30 min
  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, heptane:ethyl acetate=4:1 to 0:1)

Sources & evidence

ORD record
ord-3be1e8f5e279485d95293f177684682c
Source dataset
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08173652B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes