1,2-Dichloroethane → 5-Furan-2yl-isoxazole-3-carboxylic acid (3-imidazol-1yl-propyl)-amide

HRID 606280Notes

Reaction equation

HRID 606280 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[O:10][N:9]=[C:8]([C:11]([OH:13])=O)[CH:7]=1.[N:14]1([CH2:19][CH2:20][CH2:21][NH2:22])[CH:18]=[CH:17][N:16]=[CH:15]1.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl>CN(C=O)C>[N:14]1([CH2:19][CH2:20][CH2:21][NH:22][C:11]([C:8]2[CH:7]=[C:6]([C:2]3[O:1][CH:5]=[CH:4][CH:3]=3)[O:10][N:9]=2)=[O:13])[CH:18]=[CH:17][N:16]=[CH:15]1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 787361H-Imidazole-1-propanamineHCID 10909825-(2-Furyl)isoxazole-3-carboxylic acid

Product 1

HCID 160034475-Furan-2yl-isoxazole-3-carboxylic acid (3-imidazol-1yl-propyl)-amideYield 35%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-furan-2-yl-isoxazole-3-carboxylic acid (7 mg) and 3-imidazol-1-yl-propyl amine (0.005 mL) in DMF was added 8 mg of HOBt, 9 mg of EDC and 0.014 mL of TEA. After stirring at room temperature for 18 hrs, the reaction solution was concentrated in vacuo. The obtained concentrate was purified by preparative HPLC to afford 4 mg of 5-furan-2-yl-isoxazole-3-carboxylic acid (3-imidazol-1-yl-propyl)-amide (Yield: 35%).

Workup

  1. concentrationthe reaction solution was concentrated in vacuo
  2. concentrationThe obtained concentrate
  3. customwas purified by preparative HPLC

Sources & evidence

ORD record
ord-4dea77881e024dff89cffa0247b4acec
Source dataset
uspto-grants-2011_03
Patent number
US07915297B2

Reaction notes

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