Acetic Acid → HCID 44247704, compound

HRID 1802900Notes

Reaction equation

HRID 1802900 reaction equation
[CH:1]1([S:4]([C:7]2[C:15]([O:16][CH3:17])=[CH:14][CH:13]=[C:12]3[C:8]=2[CH:9]=[N:10][N:11]3[CH:18]([CH2:37][CH:38]2[CH2:43][CH2:42][O:41][CH2:40][CH2:39]2)[C:19](=O)[CH2:20][CH2:21][C:22]([C:24]2[CH:29]=[CH:28][C:27]([CH:30]([OH:35])[C:31]([OH:34])([CH3:33])[CH3:32])=[CH:26][N:25]=2)=O)(=[O:6])=[O:5])[CH2:3][CH2:2]1.C([O-])(=O)C.[NH4+:48].C(O)(=O)C.C(=O)([O-])O.[Na+]>C(O)C>[CH:1]1([S:4]([C:7]2[C:15]([O:16][CH3:17])=[CH:14][CH:13]=[C:12]3[C:8]=2[CH:9]=[N:10][N:11]3[CH:18]([C:19]2[NH:48][C:22]([C:24]3[N:25]=[CH:26][C:27]([CH:30]([OH:35])[C:31]([CH3:33])([OH:34])[CH3:32])=[CH:28][CH:29]=3)=[CH:21][CH:20]=2)[CH2:37][CH:38]2[CH2:39][CH2:40][O:41][CH2:42][CH2:43]2)(=[O:6])=[O:5])[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 517165Ammonium AcetateHCID 67351948HCID 67351948, compound

Product 1

HCID 44247704HCID 44247704, compoundYield 17%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 5-[4-(cyclopropylsulfonyl)-5-methoxy-1H-indazol-1-yl]-1-[5-(1,2-dihydroxy-2-methylpropyl)pyridin-2-yl]-6-(tetrahydro-2H-pyran-4-yl)hexane-1,4-dione (0.37 g), ammonium acetate (0.23 g), acetic acid (0.34 mL) and ethanol (10 mL) was stirred at room temperature for 15 hr. To the reaction mixture was added saturated aqueous sodium hydrogen carbonate solution, 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 silica gel column chromatography, and eluted from hexane-ethyl acetate (1:1-0:1, volume ratio) to give the title compound (60 mg, yield 17%) as a colorless amorphous solid. MS: 595 (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
  5. washeluted from hexane-ethyl acetate (1:1-0:1, volume ratio)

Sources & evidence

ORD record
ord-1266c38f30434e578347ebd2e538e07a
Source dataset
uspto-grants-2013_01
Patent number
US08349886B2

Reaction notes

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