2,2-Dimethylbutyryl chloride → 4-(2,2-Dimethylbutanoyl)-3-[4-(2,2,2-trifluoroethoxy)pyridin-2-yl]-1,2,4-oxadiazol-5-one

HRID 1880688Notes

Reaction equation

HRID 1880688 reaction equation
N12CCCN=C1CCCCC2.[F:12][C:13]([F:29])([F:28])[CH2:14][O:15][C:16]1[CH:21]=[CH:20][N:19]=[C:18]([C:22]2[NH:23][O:24][C:25](=[O:27])[N:26]=2)[CH:17]=1.[CH3:30][C:31]([CH3:37])([CH2:35][CH3:36])[C:32](Cl)=[O:33]>N1C=CC=CC=1>[CH3:30][C:31]([CH3:37])([CH2:35][CH3:36])[C:32]([N:26]1[C:25](=[O:27])[O:24][N:23]=[C:22]1[C:18]1[CH:17]=[C:16]([O:15][CH2:14][C:13]([F:12])([F:28])[F:29])[CH:21]=[CH:20][N:19]=1)=[O:33]

Participants

5

Reactant 3

HCID 799582,2-Dimethylbutyryl chlorideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 178517546HCID 178517546, compound

Product 1

HCID 595703914-(2,2-Dimethylbutanoyl)-3-[4-(2,2,2-trifluoroethoxy)pyridin-2-yl]-1,2,4-oxadiazol-5-oneYield 31.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To 2 ml of pyridine were added 0.25 g of 1,8-diazabicyclo[5,4,0]undec-7-ene, and 0.3 g of 3-[4-(2,2,2-trifluoroethoxy)pyridin-2-yl]-1,2,4-oxadiazol-5-one, and 0.22 g of 2,2-dimethylbutanoyl chloride was added at room temperature. After stirring for 2 hours, the mixture was further stirred at 60° C. for 2 hours. The resultant solution was concentrated, and the residue was subjected to silica gel column chromatography to obtain 0.13 g of 4-(2,2-dimethylbutanoyl)-3-[4-(2,2,2-trifluoroethoxy)pyridin-2-yl]-1,2,4-oxadiazol-5-one (present compound (25)).

Workup

  1. additionwas added at room temperature
  2. stirringthe mixture was further stirred at 60° C. for 2 hours
  3. concentrationThe resultant solution was concentrated

Sources & evidence

ORD record
ord-cbed607761d84c36b3b654cd9f753a5c
Source dataset
uspto-grants-2012_11
Patent number
US08318776B2

Reaction notes

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