2-Pyridinecarboxaldehyde → HCID 59331599, compound

HRID 1882026Notes

Reaction equation

HRID 1882026 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][S:6]([C:9]1[CH:14]=[CH:13][C:12]([CH:15]([CH2:20][CH:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)[C:16](=O)[CH:17]=[CH2:18])=[CH:11][CH:10]=1)(=[O:8])=[O:7].[N:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[CH:33]=O.C([O-])(=O)C.[NH4+:39].C(=O)([O-])O.[Na+]>C(O)C.[Cl-].C([N+]1C(C)=C(CCO)SC=1)C1C=CC=CC=1.C(O)(=O)C.C(N(CC)CC)C>[CH3:1][O:2][CH2:3][CH2:4][CH2:5][S:6]([C:9]1[CH:10]=[CH:11][C:12]([CH:15]([C:16]2[NH:39][C:33]([C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][N:27]=3)=[CH:18][CH:17]=2)[CH2:20][CH:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)=[CH:13][CH:14]=1)(=[O:8])=[O:7]

Participants

9

Reactant 4

HCID 142732-PyridinecarboxaldehydeHCID 516892Sodium BicarbonateHCID 517165Ammonium AcetateHCID 59331412HCID 59331412, compound

Product 1

HCID 59331599HCID 59331599, compoundYield 72%

Reagents, catalysts & solvents 4

HCID 28333523-Benzyl-5-(2-hydroxyethyl)-4-methylthiazolium chlorideCatalystHCID 176Acetic AcidSolventHCID 702EthanolSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of 4-{4-[(3-methoxypropyl)sulfonyl]phenyl}-5-(tetrahydro-2H-pyran-4-yl)pent-1-en-3-one (0.450 g) in ethanol (20 mL) were added pyridine-2-carbaldehyde (0.135 mL), 3-benzyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazol-3-ium chloride (35 mg) and triethylamine (0.071 mL), and the mixture was heated under reflux for 1 hr. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate:hexane=40:60-100:0, volume ratio) to give a colorless oil. To a solution of the obtained oil in acetic acid (10 mL) was added ammonium acetate (355 mg), and the mixture was stirred at 110° C. for 1.5 hr. The reaction mixture was neutralized with saturated aqueous sodium hydrogen carbonate solution, and extracted with ethyl acetate. The extract was washed successively with water and saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=40:60-100:0, volume ratio) to give the title compound (0.400 g, yield 72%) as a colorless amorphous solid. MS: 425 (MH+).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 1 hr
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (ethyl acetate:hexane=40:60-100:0, volume ratio)
  5. customto give a colorless oil
  6. extractionextracted with ethyl acetate
  7. washThe extract was washed successively with water and saturated brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=40:60-100:0, volume ratio)

Sources & evidence

ORD record
ord-4fcc1d2253904caab7c976d3c84d4186
Source dataset
uspto-grants-2012_11
Patent number
US08318746B2

Reaction notes

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