Tetrahydrofuran → HCID 178517569, compound

HRID 1880666Notes

Reaction equation

HRID 1880666 reaction equation
[O:1]1CCCC1.[F:6][C:7]1[C:8]([C:17]([NH2:19])=O)=[N:9][CH:10]=[CH:11][C:12]=1[C:13]([F:16])([F:15])[F:14].[C:20]([N:27]1C=CN=C1)(N1C=CN=C1)=[O:21].N12CCCN=C1CCCCC2>O>[F:6][C:7]1[C:8]([C:17]2[NH:19][O:1][C:20](=[O:21])[N:27]=2)=[N:9][CH:10]=[CH:11][C:12]=1[C:13]([F:16])([F:15])[F:14]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 682631,1'-CarbonyldiimidazoleHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 86647330HCID 86647330, compound

Product 1

HCID 178517569HCID 178517569, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 3 ml of tetrahydrofuran were added 0.3 g of 3-fluoro-4-trifluoromethylpyridine-2-carboxamide=oxime and 0.31 g of 1,1′-carbonyldiimidazole, and the mixture was stirred at room temperature for 2 hours. Thereafter, 0.29 g of 1,8-diazabicyclo[5,4,0]undec-7-ene was added, and the mixture was stirred for 4 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 0.19 g of 3-(3-fluoro-4-trifluoromethylpyridin-2-yl)-1,2,4-oxadiazol-5-one (present compound (50)).

Workup

  1. stirringthe mixture was stirred for 4 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-aa47defba3d940b29d574cf133b9febb
Source dataset
uspto-grants-2012_11
Patent number
US08318776B2

Reaction notes

Loading…