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

HRID 1896690Notes

Reaction equation

HRID 1896690 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-propylamine (0.005 mL) in DMF were added HOBt (8 mg), EDC (9 mg) and TEA (0.014 mL). The resulting solution was stirred at a room temperature for 18 hours, and then concentrated under reduced pressure. The resulting concentrate was purified with preparative HPLC to give 4 mg of 5-furan-2-yl-isoxazole-3-carboxylic acid (3-imidazol-1-yl-propyl)-amide (yield: 35%).

Workup

  1. concentrationconcentrated under reduced pressure
  2. concentrationThe resulting concentrate
  3. customwas purified with preparative HPLC

Sources & evidence

ORD record
ord-45056c5d997a4ac3aba2b4e33a90ddb2
Source dataset
uspto-grants-2013_08
Patent number
US08518978B2

Reaction notes

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