1,2-Dichloroethane → N-((5-(furan-2-yl)isoxazol-3-yl)methyl)-2-phenylacetamide

HRID 606287Notes

Reaction equation

HRID 606287 reaction equation
[C:1]1([CH2:7][C:8]([OH:10])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[O:11]1[CH:15]=[CH:14][CH:13]=[C:12]1[C:16]1[O:20][N:19]=[C:18]([CH2:21][NH2:22])[CH:17]=1.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl>CN(C=O)C>[O:11]1[CH:15]=[CH:14][CH:13]=[C:12]1[C:16]1[O:20][N:19]=[C:18]([CH2:21][NH:22][C:8](=[O:10])[CH2:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:17]=1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 999Phenylacetic AcidHCID 757711-HydroxybenzotriazoleHCID 70605335-(2-Furanyl)-3-isoxazolemethanamine

Product 1

HCID 45510465N-((5-(furan-2-yl)isoxazol-3-yl)methyl)-2-phenylacetamideYield 46.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 7 mg of phenylacetic acid and 5 mg of C-(5-furan-2-yl-isoxazol-3-yl)-methylamine in DMF were added 8 mg of HOBt, 9 mg of EDC and 0.02 mL of TEA. After stirring at room temperature for 18 hrs, the reaction mixture was concentrated in vacuo. The concentrate was purified by preparative HPLC to produce 4 mg of the isoxazole derivative (Yield: 35%).

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. customThe concentrate was purified by preparative HPLC

Sources & evidence

ORD record
ord-cbcdbb729c5d4f219f306fd27cd42aa3
Source dataset
uspto-grants-2011_03
Patent number
US07915297B2

Reaction notes

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