Potassium Carbonate → HCID 69112445, compound

HRID 900244Notes

Reaction equation

HRID 900244 reaction equation
[CH3:1][CH2:2][O:3][C:4]([C:6]1[NH:10][C:9]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[CH:8][N:7]=1)=[O:5].C(=O)([O-])[O-].[K+].[K+].Br[CH2:25][C:26]1[CH:30]=[C:29]([C:31]2[S:32][C:33]([Cl:36])=[CH:34][CH:35]=2)[O:28][N:27]=1>CN(C=O)C>[CH3:1][CH2:2][O:3][C:4]([C:6]1[N:10]([CH2:25][C:26]2[CH:30]=[C:29]([C:31]3[S:32][C:33]([Cl:36])=[CH:34][CH:35]=3)[O:28][N:27]=2)[C:9]([C:11]([O:13][C:14]([CH3:16])([CH3:15])[CH3:17])=[O:12])=[CH:8][N:7]=1)=[O:5]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 111501463-Bromomethyl-5-(5-chloro-thiophen-2-yl)-isoxazoleHCID 196910595-tert-Butyl 2-ethyl 1H-imidazole-2,5-dicarboxylate

Product 1

HCID 69112445HCID 69112445, compoundYield 72.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 260 mg of 3H-Imidazole-2,4-dicarboxylic acid 4-tert-butyl ester 2-ethyl ester [prepared by adopting a procedure described by J.-C. Aloup, F. Audiau, M. Barreau, D. Damour, A. Genevois-Borella, P. Jimonet, S. Mignani, Y. Ribeill PCT Int. Appl. (1996) WO96/02544 A1] in DMF (10 ml) was added potassium carbonate (178 mg) and 3-Bromomethyl-5-(5-chloro-thiophen-2-yl)-isoxazole (301 mg). The mixture was stirred for 2 h at RT. The solvent was removed in vacuo and the residue was purified by flash column chromatography on silica (n-heptane/ethyl acetate 2:1 to ethyl acetate) to provide 1-[5-(5-Chloro-thiophen-2-yl)-isoxazol-3-ylmethyl]-1H-imidazole-2,5-dicarboxylic acid 4-tert-butyl ester 2-ethyl ester (73 mg, 15%; MS (ESI+): m/e=437, chloro pattern) and 3-[5-(5-Chloro-thiophen-2-yl)-isoxazol-3-ylmethyl]-3H-imidazole-2,4-dicarboxylic acid 4-tert-butyl ester 2-ethyl ester (342 mg, 72%; MS (ESI+): m/e=437, chloro pattern) as white solids.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was purified by flash column chromatography on silica (n-heptane/ethyl acetate 2:1 to ethyl acetate)

Sources & evidence

ORD record
ord-dd9cad2af055434ba3a8b9a1099f5ba7
Source dataset
uspto-grants-2008_04
Patent number
US07358268B2

Reaction notes

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