Pyridine → HCID 86612910, compound

HRID 915884Notes

Reaction equation

HRID 915884 reaction equation
[C:1]([O:4][C@:5]1([CH3:33])[C@H:9]([O:10][C:11](=[O:13])[CH3:12])[C@@H:8]([CH2:14][O:15][C:16](=[O:18])[CH3:17])[O:7][C@H:6]1[N:19]1[CH:32]=[C:23]2[CH:24]=[CH:25][C:26]3[C:27](=O)[NH:28][N:29]=[CH:30][C:21]([C:22]=32)=[N:20]1)(=[O:3])[CH3:2].N1C=CC=CC=1.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:41]>O1CCOCC1>[CH3:33][C@@:5]1([O:4][C:1](=[O:3])[CH3:2])[C@H:9]([O:10][C:11](=[O:13])[CH3:12])[C@@H:8]([CH2:14][O:15][C:16](=[O:18])[CH3:17])[O:7][C@H:6]1[N:19]1[CH:32]=[C:23]2[CH:24]=[CH:25][C:26]3[C:27](=[S:41])[NH:28][N:29]=[CH:30][C:21]([C:22]=32)=[N:20]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 14817Phosphorus sulfide (P2S5)HCID 86612911HCID 86612911, compound

Product 1

HCID 86612910HCID 86612910, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Compound 18.1 (250 mg, 0.54 mmol) was dissolved in dioxane (5 mL) and pyridine (7 mL) was added, followed by phosphorus pentasulfide (242 mg, 0.5 mmol). The mixture was heated at reflux for 24 hr then the solvent was evaporated and the residue was washed with pyridine (3×4 mL). The combined washings were evaporated and the residue was dissolved in 50 mL CHCl3 and washed with 30 mL 10% aqueous sodium bicarbonate followed by water. The organic phase was dried over anhydrous sodium sulfate, filtered, evaporated and the residue (180 mg) containing 23.1 was used immediately in the next step.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 24 hr
  3. customthe solvent was evaporated
  4. washthe residue was washed with pyridine (3×4 mL)
  5. customThe combined washings were evaporated
  6. dissolutionthe residue was dissolved in 50 mL CHCl3
  7. washwashed with 30 mL 10% aqueous sodium bicarbonate
  8. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  9. filtrationfiltered
  10. customevaporated
  11. additionthe residue (180 mg) containing 23.1

Sources & evidence

ORD record
ord-a4932d62cb034f7092ba7f62e1f6be0b
Source dataset
uspto-grants-2007_09
Patent number
US07268119B2

Reaction notes

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