Hydrochloric Acid → HCID 178517505, compound

HRID 1880663Notes

Reaction equation

HRID 1880663 reaction equation
[F:1][C:2]1[N:7]=[C:6]([C:8]([NH2:10])=O)[CH:5]=[C:4]([C:11]([F:14])([F:13])[F:12])[CH:3]=1.[C:15](N1C=CN=C1)(N1C=CN=C1)=[O:16].[N:27]12CCCN=C1CCCCC2.Cl.[OH2:39]>O1CCCC1>[F:1][C:2]1[N:7]=[C:6]([C:8]2[NH:27][O:39][C:15](=[O:16])[N:10]=2)[CH:5]=[C:4]([C:11]([F:14])([F:13])[F:12])[CH:3]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 962WaterHCID 682631,1'-CarbonyldiimidazoleHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 86647327HCID 86647327, compound

Product 1

HCID 178517505HCID 178517505, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 5 ml of tetrahydrofuran were added 0.6 g of 6-fluoro-4-trifluoromethylpyridine-2-carboxamide=oxime and 0.61 g of 1,1′-carbonyldiimidazole, and the mixture was stirred at room temperature for 2 hours and 30 minutes. Thereafter, 0.57 g of 1,8-diazabicyclo[5,4,0]undec-7-ene was added, and the mixture was stirred for 9 hours. To the reaction solution were added water and 10% HCl, the resultant solution was extracted with ethyl acetate three times, and the organic layers were combinedmm, dried with anhydrous magnesium sulfate, and concentrated. The residue was subjected to silica gel column chromatography to obtain 0.5 g of 3-(6-fluoro-4-trifluoromethylpyridin-2-yl)-1,2,4-oxadiazol-5-one (present compound (49)).

Workup

  1. stirringthe mixture was stirred for 9 hours
  2. extractionthe resultant solution was extracted with ethyl acetate three times
  3. dry with materialdried with anhydrous magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-0ceb2f76703644adb05d0a392fe379b7
Source dataset
uspto-grants-2012_11
Patent number
US08318776B2

Reaction notes

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