3-Bromomethyl-5-(5-chloro-thiophen-2-yl)-isoxazole → HCID 21104891, compound

HRID 1354249Notes

Reaction equation

HRID 1354249 reaction equation
[Na].C([O:4][C:5]([C:7]1[N:8]=[N:9][NH:10][N:11]=1)=[O:6])C.Br[CH2:13][C:14]1[CH:18]=[C:17]([C:19]2[S:20][C:21]([Cl:24])=[CH:22][CH:23]=2)[O:16][N:15]=1>CN(C=O)C>[Cl:24][C:21]1[S:20][C:19]([C:17]2[O:16][N:15]=[C:14]([CH2:13][N:9]3[N:10]=[N:11][C:7]([C:5]([OH:4])=[O:6])=[N:8]3)[CH:18]=2)=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 111501463-Bromomethyl-5-(5-chloro-thiophen-2-yl)-isoxazoleHCID 67498453HCID 67498453, compound

Product 1

HCID 21104891HCID 21104891, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 100 mg 2H-Tetrazole-5-carboxylic acid ethyl ester sodium salt in 1 ml DMF, 59 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 at room temperature for 16 h. Then the reaction mixture was concentrated under reduced pressure. The residue was taken-up in 1 ml THF and after addtion of 1 ml of a 1M NaOH solution stirred for 16 h at RT. The mixture was acidified with half concentrated hydrochloric acid to pH 3 and the precipitate collected by filtration. The product was obtained as a white solid, which was dried under reduced pressure. Yield: 49 mg.

Workup

  1. concentrationThen the reaction mixture was concentrated under reduced pressure
  2. stirringafter addtion of 1 ml of a 1M NaOH solution stirred for 16 h at RT
  3. filtrationthe precipitate collected by filtration
  4. customThe product was obtained as a white solid, which
  5. customwas dried under reduced pressure

Sources & evidence

ORD record
ord-114c6522764b4ac597390a0a0c117194
Source dataset
uspto-grants-2007_05
Patent number
US07223780B2

Reaction notes

Loading…