Ammonia → HCID 58244093, compound

HRID 389121Notes

Reaction equation

HRID 389121 reaction equation
[NH3:1].[Cl:2][C:3]1[CH:4]=[CH:5][C:6]([O:19][C@H:20]([C:22]2[N:26]([CH3:27])[C:25]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[C:34]([F:37])([F:36])[F:35])=[N:24][N:23]=2)[CH3:21])=[C:7]([C:9]2[O:13][C:12]([C:14]([O:16]CC)=O)=[N:11][N:10]=2)[CH:8]=1.O>C(O)C>[Cl:2][C:3]1[CH:4]=[CH:5][C:6]([O:19][C@H:20]([C:22]2[N:26]([CH3:27])[C:25]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[C:34]([F:36])([F:35])[F:37])=[N:24][N:23]=2)[CH3:21])=[C:7]([C:9]2[O:13][C:12]([C:14]([NH2:1])=[O:16])=[N:11][N:10]=2)[CH:8]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 962WaterHCID 58243714HCID 58243714, compound

Product 1

HCID 58244093HCID 58244093, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 29% aqueous ammonia solution (0.3 ml) was added to a solution of ethyl 5-{5-chloro-2-[(1S)-1-{4-methyl-5-[2-(trifluoromethyl)phenyl]-4H-1,2,4-triazol-3-yl}ethoxy]phenyl}-1,3,4-oxadiazole-2-carboxylate (120 mg) in ethanol (1 ml), followed by stirring at room temperature for one hour. Water was added to the reaction solution, followed by extraction with ethyl acetate. The organic layer was washed with saturated aqueous sodium bicarbonate solution and then saturated brine in this order, and dried over anhydrous magnesium sulfate, and the solvent was then evaporated under reduced pressure. The residue was powdered with diisopropylether to obtain, as a light yellow solid, 5-{5-chloro-2-[(1S)-1-{4-methyl-5-[2-(trifluoromethyl)phenyl]-4H-1,2,4-triazol-3-yl}ethoxy]phenyl}-1,3,4-oxadiazole-2-carboxamide (86 mg).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with saturated aqueous sodium bicarbonate solution
  3. dry with materialsaturated brine in this order, and dried over anhydrous magnesium sulfate
  4. customthe solvent was then evaporated under reduced pressure

Sources & evidence

ORD record
ord-cfa6ec709dca4dbbb60b8d47440f8739
Source dataset
uspto-grants-2013_02
Patent number
US08377923B2

Reaction notes

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