Acetonitrile → HCID 68672745, compound

HRID 547994Notes

Reaction equation

HRID 547994 reaction equation
[NH:1]1[CH:5]=[N:4][CH:3]=[N:2]1.[O:6]=P(Cl)(Cl)Cl.C([O:14][C@@H:15]1[C@H:19]([O:20]C(=O)C)[C@@H:18]([CH:24]([C:26]([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)([C:35]2[CH:40]=[CH:39][C:38]([O:41][CH3:42])=[CH:37][CH:36]=2)[C:27]2[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=2)[OH:25])[S:17][C@H:16]1N1C=CC(=O)NC1=O)(=O)C.[C:57](#N)[CH3:58]>>[CH3:34][O:33][C:30]1[CH:31]=[CH:32][C:27]([C:26]([CH:24]([OH:25])[C@H:18]2[S:17][C@@H:16]([N:2]3[CH:58]=[CH:57][C:5]([NH2:1])=[N:4][C:3]3=[O:6])[C@H:15]([OH:14])[C@@H:19]2[OH:20])([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[C:35]2[CH:36]=[CH:37][C:38]([O:41][CH3:42])=[CH:39][CH:40]=2)=[CH:28][CH:29]=1

Participants

5

Reactant 4

HCID 6342Acetonitrile2×HCID 92571H-1,2,4-TriazoleHCID 24813Phosphorus oxychlorideHCID 86598590HCID 86598590, compound

Product 1

HCID 68672745HCID 68672745, compoundYield 75%

Conditions

Temperature
0 °C

Procedure

1,2,4-triazole (3.73 g, 54 mmol) was suspended in dry acetonitrile (42 mL) and cooled to 0° C. in an ice bath. POCl3 (1.44 mL, 15.4 mmol) was added drop wise with stirring. TEA (10.73 mL, 77 mmol) was added slowly with vigorous stirring and the mixture was stirred at this temperature for an additional 30 min. A solution of Compound 19 (2.43 g, 3.85 mmol) in dry acetonitrile (14 mL) was added and the mixture stirred at 0° C. for 2 h and at room temperature for 1 hr. The solvents were removed under reduced pressure and the residue taken up in ethyl acetate. The ethyl acetate solution was washed twice with saturated sodium bicarbonate solution, once with brine and dried over anhydrous sodium sulfate. The solvents were removed under reduced pressure and the residue was taken up in dioxane (40 mL) and 30% ammonium hydroxide solution (20 mL) was added. The mixture was stirred in a sealed flask overnight at room temperature. The solvents were removed under reduced pressure and the residue purified by flash chromatography (10% methanol in dichloromethane) to give Compound 20, (2.0 g) in 75% yield.

Workup

  1. stirringwith vigorous stirring
  2. stirringthe mixture was stirred at this temperature for an additional 30 min
  3. stirringthe mixture stirred at 0° C. for 2 h and at room temperature for 1 hr
  4. customThe solvents were removed under reduced pressure
  5. washThe ethyl acetate solution was washed twice with saturated sodium bicarbonate solution, once with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solvents were removed under reduced pressure
  8. addition30% ammonium hydroxide solution (20 mL) was added
  9. stirringThe mixture was stirred in a sealed flask overnight at room temperature
  10. customThe solvents were removed under reduced pressure
  11. customthe residue purified by flash chromatography (10% methanol in dichloromethane)

Sources & evidence

ORD record
ord-8d439ccc5bd147d59861e25e6ff04ed0
Source dataset
uspto-grants-2011_05
Patent number
US07939677B2

Reaction notes

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