Water → HCID 69112349, compound

HRID 900235Notes

Reaction equation

HRID 900235 reaction equation
[CH3:1][O:2][C:3]([C:5]1[NH:6][C:7]([CH2:10][O:11][CH3:12])=[N:8][CH:9]=1)=[O:4].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:20][C:21]1[CH:25]=[C:24]([C:26]2[S:27][C:28]([Cl:31])=[CH:29][CH:30]=2)[O:23][N:22]=1.O>CN(C=O)C>[CH3:1][O:2][C:3]([C:5]1[N:6]([CH2:20][C:21]2[CH:25]=[C:24]([C:26]3[S:27][C:28]([Cl:31])=[CH:29][CH:30]=3)[O:23][N:22]=2)[C:7]([CH2:10][O:11][CH3:12])=[N:8][CH:9]=1)=[O:4]

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 111501463-Bromomethyl-5-(5-chloro-thiophen-2-yl)-isoxazoleHCID 45082729Methyl 2-(methoxymethyl)-1H-imidazole-5-carboxylate

Product 1

HCID 69112349HCID 69112349, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 50 mg 2-Methoxymethyl-3H-imidazole-4-carboxylic acid methyl ester in 1 ml DMF, 95 mg caesium carbonate and 82 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: 72 mg.

Workup

  1. filtrationwas filtered through a chem elut® cartridge by elution with ethyl acetate
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was directly subjected to the subsequent saponification reaction without further purification

Sources & evidence

ORD record
ord-81d941203c2c4f43841d67435a0066b0
Source dataset
uspto-grants-2008_04
Patent number
US07358268B2

Reaction notes

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