Pyridine → HCID 86608937, compound

HRID 2112413Notes

Reaction equation

HRID 2112413 reaction equation
[NH2:1][C:2]1[C:11]2=[CH:12][N:13]([C@@H:15]3[O:28][C@H:27]([CH2:29][O:30][C:31](=[O:33])[CH3:32])[C@@H:21]([O:22][C:23](=[O:26])[CH2:24][CH3:25])[C@H:16]3[O:17][C:18](=[O:20])[CH3:19])[N:14]=[C:9]3[C:10]2=[C:4]([C:5](=O)[NH:6][N:7]=[CH:8]3)[CH:3]=1.N1C=CC=CC=1.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:42]>O1CCOCC1>[NH2:1][C:2]1[C:11]2=[CH:12][N:13]([C@@H:15]3[O:28][C@H:27]([CH2:29][O:30][C:31](=[O:33])[CH3:32])[C@@H:21]([O:22][C:23](=[O:26])[CH2:24][CH3:25])[C@H:16]3[O:17][C:18](=[O:20])[CH3:19])[N:14]=[C:9]3[C:10]2=[C:4]([C:5](=[S:42])[NH:6][N:7]=[CH:8]3)[CH:3]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 14817Phosphorus sulfide (P2S5)HCID 86608935HCID 86608935, compound

Product 1

HCID 86608937HCID 86608937, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of the compound from Step 1 (75 mg, 0.16 mmol) in dioxane (2 mL) is added pyridine (2.5 mL) followed by phosphorus pentasulfide (2 equiv). The reaction mixture is heated at reflux for 24 h. The solvent is evaporated then and the residue washed with pyridine. The combined washings are evaporated and the residue is dissolved in CHCl3 and washed with 10% aq. NaHCO3 and water and dried (Na2SO4). The evaporated residue is used as such for the next step.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureat reflux for 24 h
  3. customThe solvent is evaporated
  4. washthe residue washed with pyridine
  5. customThe combined washings are evaporated
  6. dissolutionthe residue is dissolved in CHCl3
  7. washwashed with 10% aq. NaHCO3 and water
  8. dry with materialdried (Na2SO4)

Sources & evidence

ORD record
ord-904e189cddd44d6ca78b626a9fbe2b13
Source dataset
uspto-grants-2009_04
Patent number
US07524825B2

Reaction notes

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