Water → HCID 178517508, compound

HRID 1880665Notes

Reaction equation

HRID 1880665 reaction equation
[O:1]1[CH2:5]CCC1.[F:6][C:7]1[C:8]([C:16]([F:19])([F:18])[F:17])=[CH:9][C:10]([C:13]([NH2:15])=O)=[N:11][CH:12]=1.C(N1C=CN=C1)([N:22]1C=CN=C1)=O.N12CCCN=C1CCCCC2.[OH2:43]>>[F:6][C:7]1[C:8]([C:16]([F:19])([F:18])[F:17])=[CH:9][C:10]([C:13]2[NH:22][O:43][C:5](=[O:1])[N:15]=2)=[N:11][CH:12]=1

Participants

6

Reactant 5

HCID 962WaterHCID 8028TetrahydrofuranHCID 682631,1'-CarbonyldiimidazoleHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 86647329HCID 86647329, compound

Product 1

HCID 178517508HCID 178517508, compound

Procedure

To 4 ml of tetrahydrofuran were added 0.4 g of 5-fluoro-4-trifluoromethylpyridine-2-carboxamide=oxime and 0.41 g of 1,1′-carbonyldiimidazole, and the mixture was stirred at room temperature for 2 hours. Thereafter, 0.38 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 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 0.35 g of 3-(5-fluoro-4-trifluoromethylpyridin-2-yl)-1,2,4-oxadiazol-5-one (present compound (52)).

Workup

  1. stirringthe mixture was stirred for 9 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-2caff9738e6c46778d35a75b64b41c32
Source dataset
uspto-grants-2012_11
Patent number
US08318776B2

Reaction notes

Loading…