Acetic Acid → HCID 44464405, compound

HRID 1802899Notes

Reaction equation

HRID 1802899 reaction equation
[OH:1][CH:2]([C:7]1[CH:8]=[CH:9][C:10]([C:13](=O)[CH2:14][CH2:15][C:16](=O)[CH:17]([N:25]2[C:29]3=[N:30][CH:31]=[CH:32][C:33]([O:34][CH3:35])=[C:28]3[CH:27]=[N:26]2)[CH2:18][CH:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)=[N:11][CH:12]=1)[C:3]([OH:6])([CH3:5])[CH3:4].C([O-])(=O)C.[NH4+:42].C(O)(=O)C.C(=O)([O-])O.[Na+]>C(O)C>[CH3:35][O:34][C:33]1[CH:32]=[CH:31][N:30]=[C:29]2[N:25]([CH:17]([C:16]3[NH:42][C:13]([C:10]4[N:11]=[CH:12][C:7]([CH:2]([OH:1])[C:3]([CH3:5])([OH:6])[CH3:4])=[CH:8][CH:9]=4)=[CH:14][CH:15]=3)[CH2:18][CH:19]3[CH2:24][CH2:23][O:22][CH2:21][CH2:20]3)[N:26]=[CH:27][C:28]=12

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 517165Ammonium AcetateHCID 673529111-[5-(1,2-dihydroxy-2-methylpropyl)pyridin-2-yl]-5-(4-methoxy-1H-pyrazolo[3,4-b]pyridin-1-yl)-6-(tetrahydro-2H-pyran-4-yl)hexane-1,4-dione

Product 1

HCID 44464405HCID 44464405, compoundYield 69.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1-[5-(1,2-dihydroxy-2-methylpropyl)pyridin-2-yl]-5-(4-methoxy-1H-pyrazolo[3,4-b]pyridin-1-yl)-6-(tetrahydro-2H-pyran-4-yl)hexane-1,4-dione (265 mg), ammonium acetate (200 mg), acetic acid (0.20 mL) and ethanol (10 mL) was stirred at room temperature for 6 hr. The reaction solution was poured into 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 to give the title compound (178 mg, yield 58%) as a colorless amorphous solid from the fraction eluted with ethyl acetate. MS: 492 (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-8deaa4a97be54755a495303015d00ed4
Source dataset
uspto-grants-2013_01
Patent number
US08349886B2

Reaction notes

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