Sodium Bicarbonate → HCID 59331263, compound

HRID 1882033Notes

Reaction equation

HRID 1882033 reaction equation
[CH:1]1([S:4]([C:7]2[CH:12]=[CH:11][C:10]([CH:13]([CH2:18][CH:19]3[CH2:24][CH2:23][O:22][CH2:21][CH2:20]3)[C:14](=O)[CH:15]=[CH2:16])=[CH:9][CH:8]=2)(=[O:6])=[O:5])[CH2:3][CH2:2]1.[CH:25]([C:27]1[N:32]=[CH:31][C:30]([C:33]([O:35][CH3:36])=[O:34])=[CH:29][CH:28]=1)=O.C([O-])(=O)C.[NH4+:41].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.O.C(N(CC)CC)C>[CH:1]1([S:4]([C:7]2[CH:12]=[CH:11][C:10]([CH:13]([C:14]3[NH:41][C:25]([C:27]4[N:32]=[CH:31][C:30]([C:33]([O:35][CH3:36])=[O:34])=[CH:29][CH:28]=4)=[CH:16][CH:15]=3)[CH2:18][CH:19]3[CH2:24][CH2:23][O:22][CH2:21][CH2:20]3)=[CH:9][CH:8]=2)(=[O:6])=[O:5])[CH2:3][CH2:2]1

Participants

10

Reactant 4

HCID 516892Sodium BicarbonateHCID 517165Ammonium AcetateHCID 586269Methyl 6-formylpyridine-3-carboxylateHCID 593312584-[4-(cyclopropylsulfonyl)phenyl]-5-(tetrahydro-2H-pyran-4-yl)pent-1-en-3-one

Product 1

HCID 59331263HCID 59331263, compoundYield 50.2%

Reagents, catalysts & solvents 5

HCID 28333523-Benzyl-5-(2-hydroxyethyl)-4-methylthiazolium chlorideCatalystHCID 176Acetic AcidSolventHCID 702EthanolSolventHCID 962WaterSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 4-[4-(cyclopropylsulfonyl)phenyl]-5-(tetrahydro-2H-pyran-4-yl)pent-1-en-3-one (2.47 g) in ethanol (35 mL) were added methyl 6-formylpyridine-3-carboxylate (1.29 g), 3-benzyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazol-3-ium chloride (191 mg) and triethylamine (0.397 mL), and the mixture was stirred at 70° C. for 2.5 hr. Water was added to the reaction mixture, and the mixture was 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=20:80-70:30, volume ratio) to give colorless crystals. To a solution of the obtained crystals in acetic acid (50 mL) was added ammonium acetate (3.41 g), and the mixture was stirred at 110° C. for 2 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=20:80-80:20, volume ratio), and recrystallized from hexane-ethyl acetate to give the title compound (1.76 g, yield 50%) as pale-yellow crystals. MS: 495 (MH+). melting point 150-152° C.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed successively with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=20:80-70:30, volume ratio)
  6. customto give colorless crystals
  7. stirringthe mixture was stirred at 110° C. for 2 hr
  8. extractionextracted with ethyl acetate
  9. washThe extract was washed successively with water and saturated brine
  10. dry with materialdried over anhydrous magnesium sulfate
  11. concentrationconcentrated under reduced pressure
  12. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=20:80-80:20, volume ratio)
  13. customrecrystallized from hexane-ethyl acetate

Sources & evidence

ORD record
ord-4014f5775e3b45fcb3a245653a181d77
Source dataset
uspto-grants-2012_11
Patent number
US08318746B2

Reaction notes

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