Water → [2-(5-{1-[1-methyl-5-(methylsulfonyl)-1H-pyrazol-3-yl]-2-(tetrahydro-2H-pyran-4-yl)ethyl}-1H-pyrrol-2-yl)-1,3-thiazol-5-yl]methanol

HRID 1802898Notes

Reaction equation

HRID 1802898 reaction equation
[CH3:1][N:2]1[C:6](SC)=[CH:5][C:4]([CH:9]([C:17]2[NH:21][C:20]([C:22]3[S:23][C:24]([CH2:27][OH:28])=[CH:25][N:26]=3)=[CH:19][CH:18]=2)[CH2:10][CH:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)=[N:3]1.O[O:30][S:31]([O-:33])=O.[K+].O.[C:36](=O)([O-])O.[Na+]>CO.O1CCCC1>[CH3:1][N:2]1[C:6]([S:31]([CH3:36])(=[O:33])=[O:30])=[CH:5][C:4]([CH:9]([C:17]2[NH:21][C:20]([C:22]3[S:23][C:24]([CH2:27][OH:28])=[CH:25][N:26]=3)=[CH:19][CH:18]=2)[CH2:10][CH:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)=[N:3]1

Participants

7

Reactant 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 23707502Potassium hydroxy sulfiteHCID 44464406[2-(5-{1-[1-methyl-5-(methylsulfanyl)-1H-pyrazol-3-yl]-2-(tetrahydro-2H-pyran-4-yl)ethyl}-1H-pyrrol-2-yl)-1,3-thiazol-5-yl]methanol

Product 1

HCID 44464404[2-(5-{1-[1-methyl-5-(methylsulfonyl)-1H-pyrazol-3-yl]-2-(tetrahydro-2H-pyran-4-yl)ethyl}-1H-pyrrol-2-yl)-1,3-thiazol-5-yl]methanolYield 70%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of [2-(5-{1-[1-methyl-5-(methylsulfanyl)-1H-pyrazol-3-yl]-2-(tetrahydro-2H-pyran-4-yl)ethyl}-1H-pyrrol-2-yl)-1,3-thiazol-5-yl]methanol (0.40 g), oxone (registered trade mark) (0.89 g), water (6 mL), tetrahydrofuran (6 mL) and methanol (6 mL) was stirred at room temperature for 1 hr. To the reaction mixture was added saturated aqueous sodium hydrogen carbonate, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4), and concentrated. The residue was subjected to basic silica gel column chromatography to give the title compound (0.30 g, yield 70%) as a colorless amorphous solid from the fraction eluted with tetrahydrofuran-hexane (3:1, volume ratio). MS: 451 (MH+).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with saturated brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-79cf337c34264ed3981d42f1a4424791
Source dataset
uspto-grants-2013_01
Patent number
US08349886B2

Reaction notes

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