Potassium Carbonate → 3-{1-[5-(5-chloro-thiophen-2-yl)-isoxazol-3-ylmethyl]-1H-imidazol-4-yl}-propionic acid methyl ester

HRID 900249Notes

Reaction equation

HRID 900249 reaction equation
[CH3:1][O:2][C:3](=[O:11])[CH2:4][CH2:5][C:6]1[N:7]=[CH:8][NH:9][CH:10]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:19][C:20]1[CH:24]=[C:23]([C:25]2[S:26][C:27]([Cl:30])=[CH:28][CH:29]=2)[O:22][N:21]=1>CN(C=O)C>[CH3:1][O:2][C:3](=[O:11])[CH2:4][CH2:5][C:6]1[N:7]=[CH:8][N:9]([CH2:19][C:20]2[CH:24]=[C:23]([C:25]3[S:26][C:27]([Cl:30])=[CH:28][CH:29]=3)[O:22][N:21]=2)[CH:10]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 111501463-Bromomethyl-5-(5-chloro-thiophen-2-yl)-isoxazoleHCID 178500031HCID 178500031, compound

Product 1

HCID 691120863-{1-[5-(5-chloro-thiophen-2-yl)-isoxazol-3-ylmethyl]-1H-imidazol-4-yl}-propionic acid methyl esterYield 49.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 190 mg of 3-(1H-Imidazol-4-yl)-propionic acid methyl ester (hydrochloride salt) in DMF (5 mL) was added K2CO3 (414 mg) and 3-Bromomethyl-5-(5-chloro-thiophen-2-yl)-isoxazole (278 mg). The mixture was stirred for 2 h at 70° C. After removal of the solvent in vacuo the residue was taken up in ethyl acetate. The mixture was washed with water and brine. The organic phase was dried over anhydrous MgSO4 and concentrated under reduced pressure to give crude 3-{1-[5-(5-chloro-thiophen-2-yl)-isoxazol-3-ylmethyl]-1H-imidazol-4-yl}-propionic acid methyl ester (174 mg) as a brown solid which was used in the next step without further purification.

Workup

  1. customAfter removal of the solvent in vacuo the residue
  2. washThe mixture was washed with water and brine
  3. dry with materialThe organic phase was dried over anhydrous MgSO4
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2aea88fb589a412d928943d06e3e3037
Source dataset
uspto-grants-2008_04
Patent number
US07358268B2

Reaction notes

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