Magnesium 2-(dioxidan-2-ide-1-carbonyl)benzoate--water (1/1/6) → 8-(Cyclopropylmethyl)-3-[3-methoxy-4-(2-methyl-1,3-oxazol-5-yl)phenyl]-8-[4-(methylsulfonyl)phenyl]-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridine

HRID 71097Notes

Reaction equation

HRID 71097 reaction equation
[CH:1]1([CH2:4][C:5]2([C:28]3[CH:33]=[CH:32][C:31]([S:34][CH3:35])=[CH:30][CH:29]=3)[CH2:10][CH2:9][CH2:8][N:7]3[C:11]([C:14]4[CH:19]=[CH:18][C:17]([C:20]5[O:24][C:23]([CH3:25])=[N:22][CH:21]=5)=[C:16]([O:26][CH3:27])[CH:15]=4)=[N:12][N:13]=[C:6]23)[CH2:3][CH2:2]1.[OH2:36].[OH2:37].O.O.O.O.[Mg+2].C(O[O-])(=O)C1C(=CC=CC=1)C([O-])=O>CN(C=O)C.C(OCC)(=O)C>[CH:1]1([CH2:4][C:5]2([C:28]3[CH:33]=[CH:32][C:31]([S:34]([CH3:35])(=[O:37])=[O:36])=[CH:30][CH:29]=3)[CH2:10][CH2:9][CH2:8][N:7]3[C:11]([C:14]4[CH:19]=[CH:18][C:17]([C:20]5[O:24][C:23]([CH3:25])=[N:22][CH:21]=5)=[C:16]([O:26][CH3:27])[CH:15]=4)=[N:12][N:13]=[C:6]23)[CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 21894687Magnesium 2-(dioxidan-2-ide-1-carbonyl)benzoate--water (1/1/6)2×HCID 666040818-(Cyclopropylmethyl)-3-[3-methoxy-4-(2-methyl-1,3-oxazol-5-yl)phenyl]-8-[4-(methylsulfanyl)phenyl]-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridine

Product 1

HCID 666042208-(Cyclopropylmethyl)-3-[3-methoxy-4-(2-methyl-1,3-oxazol-5-yl)phenyl]-8-[4-(methylsulfonyl)phenyl]-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridineYield 30.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 8-(cyclopropylmethyl)-3-[3-methoxy-4-(2-methyl-1,3-oxazol-5-yl)phenyl]-8-[4-(methylsulfanyl)phenyl]-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridine (86.0 mg) in DMF (1 mL) was added monoperoxyphthalic acid magnesium salt hexahydrate (87.4 mg) at 0° C., and the mixture was stirred at room temperature for 2 hr. Monoperoxyphthalic acid magnesium salt hexahydrate (87.4 mg) was added to the reaction mixture at room temperature, and the mixture was stirred at room temperature for 2 hr. The reaction mixture was diluted with ethyl acetate, the mixture was washed with aqueous sodium thiosulfate solution (1M) and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate) to give the title compound (27.8 mg).

Workup

  1. stirringthe mixture was stirred at room temperature for 2 hr
  2. washthe mixture was washed with aqueous sodium thiosulfate solution (1M)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-ff0a107a3d3e4f1aaf5015b964474c71
Source dataset
uspto-grants-2014_09
Patent number
US08822699B2

Reaction notes

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