Hydrochloric Acid → HCID 178477182, compound

HRID 1880712Notes

Reaction equation

HRID 1880712 reaction equation
[F:1][C:2]([F:20])([F:19])[C:3]([C:10]1[CH:15]=[CH:14][N:13]=[C:12](C(N)=O)[CH:11]=1)([CH3:9])[O:4][Si:5]([CH3:8])([CH3:7])[CH3:6].[C:21](N1C=CN=C1)([N:23]1C=C[N:25]=[CH:24]1)=[O:22].N12CCCN=C1CCCCC2.Cl.[OH2:45]>O1CCCC1>[F:19][C:2]([F:20])([F:1])[C:3]([C:10]1[CH:15]=[CH:14][N:13]=[C:12]([C:24]2[NH:25][O:45][C:21](=[O:22])[N:23]=2)[CH:11]=1)([CH3:9])[O:4][Si:5]([CH3:7])([CH3:6])[CH3:8]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 962WaterHCID 682631,1'-CarbonyldiimidazoleHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 86647338HCID 86647338, compound

Product 1

HCID 178477182HCID 178477182, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 4 ml of tetrahydrofuran were added 0.5 g of 4-[2,2,2-trifluoro-1-methyl-1-(trimethylsilyloxy)ethyl]pyridine-2-carboxamide=oxime and 0.42 g of 1,1′-carbonyldiimidazole, and the mixture was stirred at room temperature for 1 hour and 30 minutes. Thereafter, 0.4 g of 1,8-diazabicyclo[5,4,0]undec-7-ene was added at 0° C., and the mixture was stirred at room temperature for 4 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 0.43 g of 3-{4-[2,2,2-trifluoro-1-methyl-1-(trimethylsilyloxy)ethyl]pyridin-2-yl}-1,2,4-oxadiazol-5-one (present compound (61)).

Workup

  1. stirringthe mixture was stirred at room temperature for 4 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-e709c2366b3047f18eee85dc8dd9c966
Source dataset
uspto-grants-2012_11
Patent number
US08318776B2

Reaction notes

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