Dimethylformamide → N,5-Dimethyl-3-phenyl-4-isoxazolecarboxamide

HRID 1827315Notes

Reaction equation

HRID 1827315 reaction equation
Cl.CN.[CH:4]1[CH:5]=[CH:6][C:7]2N(O)N=N[C:8]=2[CH:9]=1.[CH3:14][CH2:15][N:16]=C=NCCCN(C)C.[CH2:25](N(CC)CC)C.[C:32](=[O:35])(O)[O-].[Na+].[CH3:37][N:38](C)[CH:39]=[O:40]>C(OCC)(=O)C>[CH3:37][NH:38][C:39]([C:14]1[C:15]([C:8]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:9]=2)=[N:16][O:35][C:32]=1[CH3:25])=[O:40]

Participants

8

Reactant 6

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 6364545Methylamine hydrochloride

Product 1

HCID 4104650N,5-Dimethyl-3-phenyl-4-isoxazolecarboxamideYield 66%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

5-Methyl-3-pyridin-4-yl-4-isoxazole-carboxylic acid (500 mg, 2.5 mmols) obtained in Reference Example 5 was dissolved in N,N-dimethylformamide (10 ml), and methylamine hydrochloride (333 mg, 4.9 mmols), HOBt (496 mg, 3.7 mmols), WSC (702 mg, 3.7 mols) and triethylamine (1.02 ml, 7.3 mmols) were added to the solution. The reaction mixture was stirred at room temperature for 5 hours. The reaction liquid was transferred into aqueous saturated sodium bicarbonate solution, and ethyl acetate was added thereto for organic layer extraction. The liquid extract was washed with aqueous saturated sodium bicarbonate solution, and the organic layer was dried with magnesium sulfate. Then, the solvent was removed under reduced pressure, and the resulting residue was purified through silica gel column chromatography to obtain the entitled compound (360 mg, yield 66%).

Workup

  1. customThe reaction liquid
  2. additionwas added
  3. extractionfor organic layer extraction
  4. extractionThe liquid extract
  5. washwas washed with aqueous saturated sodium bicarbonate solution
  6. dry with materialthe organic layer was dried with magnesium sulfate
  7. customThen, the solvent was removed under reduced pressure
  8. customthe resulting residue was purified through silica gel column chromatography

Sources & evidence

ORD record
ord-bdd98dfbb32b4f129110f564853dcb45
Source dataset
uspto-grants-2006_05
Patent number
US07053219B2

Reaction notes

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