Pyridine → HCID 21480487, compound

HRID 1490049Notes

Reaction equation

HRID 1490049 reaction equation
OCCN1C(CO)CC2[S:12][C:13]([S:15]([NH2:18])(=[O:17])=[O:16])=CC=2S1(=O)=O.[C:21]1(C)[CH:26]=[CH:25][C:24]([S:27](Cl)(=[O:29])=[O:28])=[CH:23][CH:22]=1.COCC[NH2:36].[C:37](=[O:40])([O-])[O-].[Ba+2].[N:42]1[CH:47]=[CH:46]C=[CH:44][CH:43]=1>[Cl-].[Na+].O>[CH3:37][O:40][CH2:44][CH2:43][N:42]1[CH2:47][CH2:46][N:18]2[S:15](=[O:17])(=[O:16])[C:13]3[S:12][C:24]([S:27]([NH2:36])(=[O:28])=[O:29])=[CH:25][C:26]=3[CH2:21][CH:22]2[CH2:23]1

Participants

7

Reactant 5

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 80182-MethoxyethylamineHCID 10563Barium CarbonateHCID 67711344HCID 67711344, compound

Product 1

HCID 21480487HCID 21480487, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Procedure

To a stirred solution of the product from Step F (2.50 g, 7.3 mmol) in pyridine (10.0 mL) was added p-toluenesulfonyl chloride (4.50 g, 23.0 mmol) at room temperature. After 16 h, brine (50 mL) was added and the mixture extracted with ethyl acetate (4×50 mL). The combined extracts were washed with brine (20 mL), dried (MgSO4), and evaporated. The residue was dissolved in THF (10 mL) and 2-methoxyethylamine (6.40 mL, 73.0 mmol) was added followed by solid barium carbonate (4.30 g, 22.0 mmol); this mixture was refluxed for 36 h. The excess of amine and THF were removed by evaporation, a saturated aqueous solution of ammonium chloride (50 mL) was added and the mixture was extracted with ethyl acetate (4×50 mL). The combined extracts were washed with brine (20 mL), dried (MgSO4), and evaporated to a residue which was purified by column chromatography (silica, gradient, 30% to 60% ethyl acetate-hexane) to give a solid (1.25 g, 45%). Recrystallization from methanol gave white crystals (0.75 g): mp. 224°-225° C.

Workup

  1. extractionthe mixture extracted with ethyl acetate (4×50 mL)
  2. washThe combined extracts were washed with brine (20 mL)
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. dissolutionThe residue was dissolved in THF (10 mL)
  6. temperaturethis mixture was refluxed for 36 h
  7. customThe excess of amine and THF were removed by evaporation
  8. additiona saturated aqueous solution of ammonium chloride (50 mL) was added
  9. extractionthe mixture was extracted with ethyl acetate (4×50 mL)
  10. washThe combined extracts were washed with brine (20 mL)
  11. dry with materialdried (MgSO4)
  12. customevaporated to a residue which
  13. customwas purified by column chromatography (silica, gradient, 30% to 60% ethyl acetate-hexane)

Sources & evidence

ORD record
ord-957de631263b4f7d88bc76a489ff5398
Source dataset
uspto-grants-1997_10
Patent number
US05681834

Reaction notes

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