1,2-Dichloroethane → N-(5-furan-2-yl-isoxazol-3-yl)-3-pyridin-2-yl-acrylamide

HRID 606282Notes

Reaction equation

HRID 606282 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]=[CH:8][C:9]([OH:11])=O.[O:12]1[CH:16]=[CH:15][CH:14]=[C:13]1[C:17]1[O:21][N:20]=[C:19]([NH2:22])[CH:18]=1.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl>CN(C=O)C>[O:12]1[CH:16]=[CH:15][CH:14]=[C:13]1[C:17]1[O:21][N:20]=[C:19]([NH:22][C:9](=[O:11])[CH:8]=[CH:7][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)[CH:18]=1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 2478243-(2-Pyridyl)acrylic acidHCID 132302595-(Furan-2-yl)isoxazol-3-amine

Product 1

HCID 67047568N-(5-furan-2-yl-isoxazol-3-yl)-3-pyridin-2-yl-acrylamideYield 36%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 6 mg of 3-pyridin-2-yl-acrylic acid and 6 mg of 5-furan-2-yl-isoxazol-3-ylamine in DMF were added 8 mg of HOBt, 9 mg of EDC and 0.014 mL of TEA. The reaction solution was stirred for 18 hrs at room temperature, followed by concentration under reduced pressure. The concentrate was purified by preparative HPLC to provide 4 mg of N-(5-furan-2-yl-isoxazol-3-yl)-3-pyridin-2-yl-acrylamide. (Yield: 36%).

Workup

  1. concentrationfollowed by concentration under reduced pressure
  2. customThe concentrate was purified by preparative HPLC

Sources & evidence

ORD record
ord-b668bced9f59491b94c4f4a2666273b0
Source dataset
uspto-grants-2011_03
Patent number
US07915297B2

Reaction notes

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