Potassium Carbonate → HCID 70160415, compound

HRID 2227275Notes

Reaction equation

HRID 2227275 reaction equation
COP([CH2:7][C:8](=[O:25])[CH2:9][N:10]1[C@H:14]([CH3:15])[CH2:13][C@H:12]([NH:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C:11]1=[O:24])(=O)OC.C(=O)([O-])[O-].[K+].[K+].[CH3:32][O:33][C:34]1[N:39]=[CH:38][C:37]([CH:40]=O)=[CH:36][CH:35]=1>CN(C)C=O.C(OCC)(=O)C>[C:20]([O:19][C:17](=[O:18])[NH:16][C@H:12]1[CH2:13][C@@H:14]([CH3:15])[N:10]([CH2:9][C:8](=[O:25])[CH:7]=[CH:40][C:37]2[CH:38]=[N:39][C:34]([O:33][CH3:32])=[CH:35][CH:36]=2)[C:11]1=[O:24])([CH3:21])([CH3:22])[CH3:23]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 33645766-Methoxypyridine-3-carbaldehydeHCID 86758298HCID 86758298, compound

Product 1

HCID 70160415HCID 70160415, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
82.5 °C

Procedure

A stirred suspension of 4-3 (190 mg, 0.50 mmol), potassium carbonate (104 mg, 0.75 mmol), and 6-methoxy-pyridine-3-carboxaldehyde (for preparation, see U.S. Pat. No. 6,048,861, which is incorporated by reference herein in its entirety) (69 mg, 0.50 mmol) in N,N-dimethylformamide (2 mL) was heated at 80-85° C. for 3 hours and then cooled to ambient temperature. The reaction mixture was diluted with ethyl acetate, washed with saturated aqueous sodium hydrogen carbonate, saturated aqueous sodium chloride, dried over magnesium sulfate, and filtered. Following evaporative removal of the solvent, the residue was purified by flash column chromatography (silica gel, 95:5% ethyl acetate/methanol) to give 4-4 as a colorless oil.

Workup

  1. customfor preparation
  2. temperaturecooled to ambient temperature
  3. washwashed with saturated aqueous sodium hydrogen carbonate, saturated aqueous sodium chloride
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customremoval of the solvent
  7. customthe residue was purified by flash column chromatography (silica gel, 95:5% ethyl acetate/methanol)

Sources & evidence

ORD record
ord-6b87f5fa04094d1d92ecfb1ba3b9afa3
Source dataset
uspto-grants-2002_07
Patent number
US06413955B1

Reaction notes

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