Methanol → 2-[5-[2-[[4-(Methylthio)phenyl]amino]-4-pyridyl]-1,3,4-oxadiazol-2-yl]propan-2-ol

HRID 452773Notes

Reaction equation

HRID 452773 reaction equation
C([O:4][C:5]([CH3:27])([C:7]1[O:8][C:9]([C:12]2[CH:17]=[CH:16][N:15]=[C:14]([NH:18][C:19]3[CH:24]=[CH:23][C:22]([S:25][CH3:26])=[CH:21][CH:20]=3)[CH:13]=2)=[N:10][N:11]=1)[CH3:6])(=O)C.[OH-].[Na+].O1CCCC1.CO>C(OCC)(=O)C>[CH3:26][S:25][C:22]1[CH:23]=[CH:24][C:19]([NH:18][C:14]2[CH:13]=[C:12]([C:9]3[O:8][C:7]([C:5]([OH:4])([CH3:6])[CH3:27])=[N:11][N:10]=3)[CH:17]=[CH:16][N:15]=2)=[CH:20][CH:21]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 686643731-Methyl-1-[5-[2-[[4-(methylthio)phenyl]amino]-4-pyridyl]-1,3,4-oxadiazol-2-yl]ethyl acetate

Product 1

HCID 686645372-[5-[2-[[4-(Methylthio)phenyl]amino]-4-pyridyl]-1,3,4-oxadiazol-2-yl]propan-2-olYield 36%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1-methyl-1-[5-[2-[[4-(methylthio)phenyl]amino]-4-pyridyl]-1,3,4-oxadiazol-2-yl]ethyl acetate (192 mg, 4.99 mmol), 1 M aqueous sodium hydroxide solution (5 mL), tetrahydrofuran (5 mL) and methanol (5 mL) was stirred at room temperature for 1.5 hr. The reaction mixture was diluted with ethyl acetate, washed with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (hexane/ethyl acetate=10/1-0/1) and recrystallized from hexane/ethyl acetate to give the title compound (61.2 mg, yield 36%) as yellow crystals.

Workup

  1. washwashed with water and saturated brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by basic silica gel column chromatography (hexane/ethyl acetate=10/1-0/1)
  5. customrecrystallized from hexane/ethyl acetate

Sources & evidence

ORD record
ord-1466ec0cb3e944c8bc17c97d957ebcd2
Source dataset
uspto-grants-2013_07
Patent number
US08492378B2

Reaction notes

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