Water → HCID 58243771, compound

HRID 389128Notes

Reaction equation

HRID 389128 reaction equation
[CH3:1][C:2]([C:19]1[N:23]([CH3:24])[C:22]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[C:31]([F:34])([F:33])[F:32])=[N:21][N:20]=1)([O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[O:15][N:14]=[C:13](C(O)=O)[N:12]=2)=[CH:7][CH:6]=1)[CH3:3].O>CS(C)=O>[CH3:3][C:2]([C:19]1[N:23]([CH3:24])[C:22]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[C:31]([F:33])([F:34])[F:32])=[N:21][N:20]=1)([O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[O:15][N:14]=[CH:13][N:12]=2)=[CH:7][CH:6]=1)[CH3:1]

Participants

4

Reactant 2

HCID 962WaterHCID 58244209HCID 58244209, compound

Product 1

HCID 58243771HCID 58243771, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
60 °C

Procedure

5-[4-(1-methyl-1-{4-methyl-5-[2-(trifluoromethyl)phenyl]-4H-1,2,4-triazol-3-yl}ethoxy)phenyl]-1,2,4-oxadiazole-3-carboxylic acid (172 mg) was dissolved in DMSO (1 ml), followed by stirring at 60° C. for 2 hours. The reaction solution was cooled to room temperature and water was added thereto, followed by stirring for 15 minutes. The formed solid was collected by filtration and washed with water. The resulting solid was dissolved in ethyl acetate and washed with water and then saturated brine in this order. The organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The resulting solid was washed with ethyl acetate to obtain 5-[4-(1-methyl-1-{4-methyl-5-[2-(trifluoromethyl)phenyl]-4H-1,2,4-triazol-3-yl}ethoxy)phenyl]-1,2,4-oxadiazole (103 mg), as a white solid.

Workup

  1. temperatureThe reaction solution was cooled to room temperature
  2. stirringby stirring for 15 minutes
  3. filtrationThe formed solid was collected by filtration
  4. washwashed with water
  5. dissolutionThe resulting solid was dissolved in ethyl acetate
  6. washwashed with water
  7. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. washThe resulting solid was washed with ethyl acetate

Sources & evidence

ORD record
ord-5dad608026674895ad6cb5b13d6ae587
Source dataset
uspto-grants-2013_02
Patent number
US08377923B2

Reaction notes

Loading…