Water → HCID 178517503, compound

HRID 1880667Notes

Reaction equation

HRID 1880667 reaction equation
[O:1]1[CH2:5]CCC1.[CH:6]1([C:9]2[N:14]=[C:13]([C:15]([NH2:17])=O)[CH:12]=[C:11]([C:18]([F:21])([F:20])[F:19])[CH:10]=2)[CH2:8][CH2:7]1.C(N1C=CN=C1)([N:24]1C=CN=C1)=O.N12CCCN=C1CCCCC2.[OH2:45]>>[CH:6]1([C:9]2[N:14]=[C:13]([C:15]3[NH:24][O:45][C:5](=[O:1])[N:17]=3)[CH:12]=[C:11]([C:18]([F:21])([F:20])[F:19])[CH:10]=2)[CH2:8][CH2:7]1

Participants

6

Reactant 5

HCID 962WaterHCID 8028TetrahydrofuranHCID 682631,1'-CarbonyldiimidazoleHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 86647331HCID 86647331, compound

Product 1

HCID 178517503HCID 178517503, compound

Procedure

To 5 ml of tetrahydrofuran were added 0.6 g of 6-cyclopropyl-4-trifluoromethylpyridine-2-carboxamide=oxime and 0.56 g of 1,1′-carbonyldiimidazole, and the mixture was stirred at room temperature for 2 hours. Thereafter, 0.52 g of 1,8-diazabicyclo[5,4,0]undec-7-ene was added, and the mixture was stirred for 10 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 0.52 g of 3-(6-cyclopropyl-4-trifluoromethylpyridin-2-yl)-1,2,4-oxadiazol-5-one (present compound (53)).

Workup

  1. stirringthe mixture was stirred for 10 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-79831ee7a67d4b1d81fc0c365c8daf43
Source dataset
uspto-grants-2012_11
Patent number
US08318776B2

Reaction notes

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