Diisopropylcarbodiimide → N-[5-(4-fluoro-phenyl)-isoxazol-3-yl]-malonamic acid ethyl ester

HRID 1665687Notes

Reaction equation

HRID 1665687 reaction equation
C(N=C=NC(C)C)(C)C.[F:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[O:21][N:20]=[C:19]([NH2:22])[CH:18]=2)=[CH:13][CH:12]=1.[CH2:23]([O:25][C:26](=[O:31])[CH2:27][C:28](O)=[O:29])[CH3:24]>C1COCC1.C(OCC)(=O)C>[CH2:23]([O:25][C:26](=[O:31])[CH2:27][C:28]([NH:22][C:19]1[CH:18]=[C:17]([C:14]2[CH:13]=[CH:12][C:11]([F:10])=[CH:16][CH:15]=2)[O:21][N:20]=1)=[O:29])[CH3:24]

Participants

6

Reactant 3

HCID 12734DiisopropylcarbodiimideHCID 70615Monoethyl malonateHCID 132004245-(4-Fluorophenyl)-1,2-oxazol-3-amine

Product 1

HCID 57875802N-[5-(4-fluoro-phenyl)-isoxazol-3-yl]-malonamic acid ethyl esterYield 832.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Diisopropyl carbodiimide (0.07 mL, 0.45 mmol) and 5-(4-fluoro-phenyl)-isoxazol-3-ylamine (67 mg, 0.037 mmol) were added to a stirred solution of malonic acid monoethyl ester (50 mg, 0.37 mmol) in THF (1 mL) and stirring was continued at reflux temperature for 4 hrs. The mixture was concentrated under reduced pressure. The residue obtained was diluted with ethyl acetate and washed with water, followed by brine solution. The organic layer collected was dried over Na2SO4 and concentrated under reduced pressure to afford 90 mg (81.8% Yield) of N-[5-(4-fluoro-phenyl)-isoxazol-3-yl]-malonamic acid ethyl ester.

Workup

  1. temperatureat reflux temperature for 4 hrs
  2. concentrationThe mixture was concentrated under reduced pressure
  3. customThe residue obtained
  4. washwashed with water
  5. customThe organic layer collected
  6. dry with materialwas dried over Na2SO4
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-bc9c2154121c46a0bc19592d5d1bb707
Source dataset
uspto-grants-2011_10
Patent number
US08039463B2

Reaction notes

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