Pyridine → HCID 10839202, compound

HRID 1872087Notes

Reaction equation

HRID 1872087 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][CH:15]([CH3:17])[CH3:16])=[CH:10][CH:9]=2)[C:5]([S:18]([NH:21][C:22]2[O:26][N:25]=[C:24]([CH3:27])[C:23]=2[CH3:28])(=[O:20])=[O:19])=[CH:4][CH:3]=1.N1C=CC=CC=1.[C:35](Cl)(=[O:42])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>CC(C)=O>[CH3:27][C:24]1[C:23]([CH3:28])=[C:22]([NH:21][S:18]([C:5]2[CH:4]=[CH:3][C:2]([NH:1][C:35](=[O:42])[C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)=[CH:7][C:6]=2[C:8]2[CH:13]=[CH:12][C:11]([CH2:14][CH:15]([CH3:16])[CH3:17])=[CH:10][CH:9]=2)(=[O:20])=[O:19])[O:26][N:25]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 7412Benzoyl chlorideHCID 10668636HCID 10668636, compound

Product 1

HCID 10839202HCID 10839202, compoundYield 19.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of the compound of Example 43 (0.4 g, 1.0 mmol) and pyridine (0.082 mL, 1.0 mmol) in acetone (3 mL) was added benzoyl chloride (0.12 mL, 1.0 mmol). The mixture was stirred for 18 hours and concentrated. The residue was dissolved in methanol (50 mL) and a 5% solution of sodium hydrogen carbonate in water (10 mL) was added. The solution was stirred for 1 hour and the methanol was removed under vacuum. The aqueous residue was acidified to pH 3 with 6N aqueous hydrochloric acid and extracted three times with ethyl acetate. The combined organic phases were washed with water and brine, and dried (magnesium sulfate). The residue was chromatographed on silica with (1:1) ethyl acetate:hexanes to afford 98 mg (19%) of the title compound as a tan solid, mp 207-211° C.

Workup

  1. concentrationconcentrated
  2. dissolutionThe residue was dissolved in methanol (50 mL)
  3. additiona 5% solution of sodium hydrogen carbonate in water (10 mL) was added
  4. stirringThe solution was stirred for 1 hour
  5. customthe methanol was removed under vacuum
  6. extractionextracted three times with ethyl acetate
  7. washThe combined organic phases were washed with water and brine
  8. dry with materialdried (magnesium sulfate)
  9. customThe residue was chromatographed on silica with (1:1) ethyl acetate

Sources & evidence

ORD record
ord-5864cc1636274051895b05e40d162bd4
Source dataset
uspto-grants-2000_08
Patent number
US06107320

Reaction notes

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