Hydrochloric Acid → HCID 178466936, compound

HRID 1880713Notes

Reaction equation

HRID 1880713 reaction equation
[F:1][C:2]([F:23])([F:22])[C:3]([C:10]1[CH:15]=[CH:14][N:13]=[C:12]([C:16]2[NH:17][O:18][C:19](=[O:21])[N:20]=2)[CH:11]=1)([CH3:9])[O:4][Si](C)(C)C.C([N+](CCCC)(CCCC)CCCC)CCC.[F-].Cl>O.O1CCCC1>[F:23][C:2]([F:1])([F:22])[C:3]([C:10]1[CH:15]=[CH:14][N:13]=[C:12]([C:16]2[NH:17][O:18][C:19](=[O:21])[N:20]=2)[CH:11]=1)([CH3:9])[OH:4]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 16028TetrabutylammoniumHCID 28179Fluoride IonHCID 178477182HCID 178477182, compound

Product 1

HCID 178466936HCID 178466936, compoundYield 3.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To 3 ml of tetrahydrofuran was added 12 g of 3-{4-[2,2,2-trifluoro-1-methyl-1-(trimethylsilyloxy)ethyl]pyridin-2-yl}-1,2,4-oxadiazol-5-one, and 1.3 ml of tetrabutylammonium=fluoride (1M tetrahydrofuran solution) was added at 0° C. After stirring at room temperature for 4 hours, water and 10% HCl were added to the reaction 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 0.29 g of 3-[4-(2,2,2-trifluoro-1-methyl-1-hydroxyethyl)pyridin-2-yl]-1,2,4-oxadiazol-5-one (present compound (62)).

Workup

  1. additionwas added at 0° C
  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-3e4623db73204c90989cc7c9281dffb4
Source dataset
uspto-grants-2012_11
Patent number
US08318776B2

Reaction notes

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