Water → HCID 178426042, compound

HRID 1880668Notes

Reaction equation

HRID 1880668 reaction equation
[O:1]1[CH2:5]CCC1.[CH3:6][C:7]1[N:12]=[C:11]([C:13]([NH2:15])=O)[CH:10]=[C:9]([C:16]([F:19])([F:18])[F:17])[CH:8]=1.C(N1C=CN=C1)([N:22]1C=CN=C1)=O.N12CCCN=C1CCCCC2.[OH2:43]>>[CH3:6][C:7]1[N:12]=[C:11]([C:13]2[NH:22][O:43][C:5](=[O:1])[N:15]=2)[CH:10]=[C:9]([C:16]([F:19])([F:18])[F:17])[CH:8]=1

Participants

6

Reactant 5

HCID 962WaterHCID 8028TetrahydrofuranHCID 682631,1'-CarbonyldiimidazoleHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 866473326-Methyl-4-trifluoromethylpyridine-2-carboxamide

Product 1

HCID 178426042HCID 178426042, compound

Procedure

To 3 ml of tetrahydrofuran were added 0.74 g of 6-methyl-4-trifluoromethylpyridine-2-carboxamide=oxime and 0.41 g of 1,1′-carbonyldiimidazole, and the mixture was stirred at room temperature for 1 hour and 30 minutes. Thereafter, 0.39 g of 1,8-diazabicyclo[5,4,0]undec-7-ene was added, and the mixture was stirred for 12 hours. To the reaction solution were added water and a 10% aqueous HCl solution, the resultant solution was extracted with ethyl acetate three times, and the organic layers were combined, dried with anhydrous magnesium sulfate, and concentrated. The residue was subjected to silica gel column chromatography to obtain 0.6 g of 3-(6-methyl-4-trifluoromethylpyridin-2-yl)-1,2,4-oxadiazol-5-one (present compound (54)).

Workup

  1. stirringthe mixture was stirred for 12 hours
  2. extractiona 10% aqueous HCl solution, the resultant solution was extracted with ethyl acetate three times
  3. dry with materialdried with anhydrous magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-d060f35d747a4d88b74e31ea397f088f
Source dataset
uspto-grants-2012_11
Patent number
US08318776B2

Reaction notes

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