Hydrochloric Acid → HCID 178517528, compound

HRID 1880709Notes

Reaction equation

HRID 1880709 reaction equation
[F:1][C:2]([F:18])([F:17])[CH:3]([C:5]1[CH:10]=[CH:9][N:8]=[C:7]([C:11]2[NH:12][O:13][C:14](=[O:16])[N:15]=2)[CH:6]=1)[OH:4].C(N(CC)CC)C.[OH2:26].Cl>CS(C)=O>[F:18][C:2]([F:1])([F:17])[C:3]([C:5]1[CH:10]=[CH:9][N:8]=[C:7]([C:11]2[NH:12][O:13][C:14](=[O:16])[N:15]=2)[CH:6]=1)([OH:26])[OH:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 8471TriethylamineHCID 178517526HCID 178517526, compound

Product 1

HCID 178517528HCID 178517528, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

To 2 ml of dimethyl sulfoxide were added 0.3 g of 3-[4-(2,2,2-trifluoro-1-hydroxyethyl)pyridin-2-yl]-1,2,4-oxadiazol-5-one and 0.48 ml of triethylamine, and 1 ml of a solution of 0.55 g of sulfur-trioxide-pyridine complex in dimethyl sulfoxide was added dropwise. After stirring for 8 hours, 0.17 g of sulfur-trioxide-pyridine complex was added, and the mixture was further stirred for 7 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 0.18 g of 3-{4-[2,2,2-trifluoro-1,1-dihydroxyethyl]pyridin-2-yl}-1,2,4-oxadiazol-5-one (present compound (58)).

Workup

  1. additionwas added dropwise
  2. addition0.17 g of sulfur-trioxide-pyridine complex was added
  3. stirringthe mixture was further stirred for 7 hours
  4. extractionthe resultant solution was extracted with ethyl acetate three times
  5. dry with materialdried with anhydrous magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-d3f9f979a9024e29a1eb8cda8d47ab07
Source dataset
uspto-grants-2012_11
Patent number
US08318776B2

Reaction notes

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