Water → 3-[5-(5-Chloro-thiophen-2-yl)-isoxazol-3-ylmethyl]-3H-imidazole-4-carboxylic acid methyl ester
Reaction equation
[CH3:1][O:2][C:3]([C:5]1[NH:6][CH:7]=[N:8][CH:9]=1)=[O:4].Br[CH2:11][C:12]1[CH:16]=[C:15]([C:17]2[S:18][C:19]([Cl:22])=[CH:20][CH:21]=2)[O:14][N:13]=1.O>CN(C=O)C>[CH3:1][O:2][C:3]([C:5]1[N:6]([CH2:11][C:12]2[CH:16]=[C:15]([C:17]3[S:18][C:19]([Cl:22])=[CH:20][CH:21]=3)[O:14][N:13]=2)[CH:7]=[N:8][CH:9]=1)=[O:4]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 250 mg 3H-Imidazole-4-carboxylic acid methyl ester in 2 ml DMF 273 mg potassium carbonate and 607 mg 3-Bromomethyl-5-(5-chloro-thiophen-2-yl)-isoxazole [prepared by adopting a procedure described by Ewing, William R.; Becker, Michael R.; Choi-Sledeski, Yong Mi; Pauls, Heinz W.; He, Wei; Condon, Stephen M.; Davis, Roderick S.; Hanney, Barbara A.; Spada, Alfred P.; Burns, Christopher J.; Jiang, John Z.; Li, Aiwen; Myers, Michael R.; Lau, Wan F.; Poli, Gregory B; PCT Int. Appl. (2001), 460 pp. WO 0107436 A2] were added and the mixture was stirred for 2 h at RT. After addition of 5 ml water the mixture was filtered through a chem elut® cartridge by elution with ethyl acetate and then concentrated under reduced pressure. The residue was directly subjected to the subsequent saponification reaction without further purification. Yield: 288 mg
Workup
- filtrationwas filtered through a chem elut® cartridge by elution with ethyl acetate
- concentrationconcentrated under reduced pressure
- customThe residue was directly subjected to the subsequent saponification reaction without further purification
Sources & evidence
- ORD record
- ord-023f2c7cc8104219ac5ccb93c81ed0a0
- Source dataset
- uspto-grants-2008_04
- Patent number
- US07358268B2
Reaction notes
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