Hydrochloric Acid → HCID 178517502, compound

HRID 1880710Notes

Reaction equation

HRID 1880710 reaction equation
[F:1][C:2]([F:16])([C:7]1[CH:12]=[CH:11][N:10]=[C:9]([C:13]([NH2:15])=O)[CH:8]=1)[C:3]([F:6])([F:5])[F:4].[C:17](N1C=CN=C1)(N1C=CN=C1)=[O:18].[N:29]12CCCN=C1CCCCC2.Cl.[OH2:41]>O1CCCC1>[F:1][C:2]([F:16])([C:7]1[CH:12]=[CH:11][N:10]=[C:9]([C:13]2[NH:29][O:41][C:17](=[O:18])[N:15]=2)[CH:8]=1)[C:3]([F:6])([F:5])[F:4]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 962WaterHCID 682631,1'-CarbonyldiimidazoleHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 86647336HCID 86647336, compound

Product 1

HCID 178517502HCID 178517502, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 8 ml of tetrahydrofuran were added 0.9 g of 4-pentafluoroethylpyridine-2-carboxamide=oxime and 0.95 g of 1,1′-carbonyldiimidazole, and the mixture was stirred at room temperature for 2 hours. Thereafter, 0.89 g of 1,8-diazabicyclo[5,4,0]undec-7-ene was added at 0° C., and the mixture was stirred for 2 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 combined, dried with anhydrous magnesium sulfate, and concentrated. The residue was subjected to silica gel column chromatography to obtain 0.9 g of 3-(4-pentafluoroethylpyridin-2-yl)-1,2,4-oxadiazol-5-one (present compound (59)).

Workup

  1. stirringthe mixture was stirred for 2 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-516b606c906948fbbb553bc0f3fb2a48
Source dataset
uspto-grants-2012_11
Patent number
US08318776B2

Reaction notes

Loading…