Water → HCID 59331369, compound

HRID 1882094Notes

Reaction equation

HRID 1882094 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[NH:9][C:10]([CH:13]([C:21]3[CH:26]=[CH:25][C:24](SC)=[CH:23][N:22]=3)[CH2:14][CH:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)=[CH:11][CH:12]=2)=[N:6][CH:7]=1.O1CCC[CH2:30]1.O.O[O:36][S:37]([O-:39])=O.[K+]>C(OCC)(=O)C.CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[NH:9][C:10]([CH:13]([C:21]3[CH:26]=[CH:25][C:24]([S:37]([CH3:30])(=[O:39])=[O:36])=[CH:23][N:22]=3)[CH2:14][CH:15]3[CH2:16][CH2:17][O:18][CH2:19][CH2:20]3)=[CH:11][CH:12]=2)=[N:6][CH:7]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 23707502Potassium hydroxy sulfiteHCID 68433023HCID 68433023, compound

Product 1

HCID 59331369HCID 59331369, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 5-chloro-2-(5-{1-[5-(methylsulfanyl)pyridin-2-yl]-2-(tetrahydro-2H-pyran-4-yl)ethyl}-1H-pyrrol-2-yl)pyridine (117 mg), tetrahydrofuran (2 mL), water (2 mL) and methanol (2 mL) was added Oxone (registered trademark) (207 mg), and the mixture was stirred at room temperature for 4 hr. The reaction mixture was diluted with ethyl acetate, and washed with saturated aqueous sodium hydrogen carbonate solution. The ethyl acetate layer was dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography, and the title compound (64.6 mg, yield 52%) was obtained as a white amorphous solid from a fraction eluted with ethyl acetate-hexane (2:1, volume ratio). MS: 446 (MH+).

Workup

  1. washwashed with saturated aqueous sodium hydrogen carbonate solution
  2. dry with materialThe ethyl acetate layer was dried (MgSO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-84b32458501143c8af76d8637f1b58da
Source dataset
uspto-grants-2012_11
Patent number
US08318746B2

Reaction notes

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