Tetrahydrofuran → HCID 59769545, compound

HRID 2096081Notes

Reaction equation

HRID 2096081 reaction equation
C(N(CC)CC)C.[C:8]([O:11][CH2:12][CH2:13][N:14]([C:21]([N:23]1[C:27]2[CH:28]=[C:29](OC)[CH:30]=[CH:31][C:26]=2[N:25]=[C:24]1[S:34]([CH2:36][C:37]1[C:42]([CH3:43])=[C:41]([O:44][CH3:45])[C:40]([CH3:46])=[CH:39][N:38]=1)=[O:35])=[O:22])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)(=[O:10])[CH3:9].[O:47]1CCC[CH2:48]1>>[C:8]([O:11][CH2:12][CH2:13][N:14]([C:21]([N:23]1[C:27]2[CH:28]=[CH:29][C:30]([O:47][CH3:48])=[CH:31][C:26]=2[N:25]=[C:24]1[S:34]([CH2:36][C:37]1[C:42]([CH3:43])=[C:41]([O:44][CH3:45])[C:40]([CH3:46])=[CH:39][N:38]=1)=[O:35])=[O:22])[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)(=[O:10])[CH3:9]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 66894587HCID 66894587, compound

Product 1

HCID 59769545HCID 59769545, compound

Procedure

To a solution of bis(trichloromethyl)carbonate (0.291 g) in tetrahydrofuran (10 mL) was added dropwise a solution of pyridine (0.243 mL) in tetrahydrofuran (1 mL) under ice-cooling. The reaction solution was stirred for 30 minutes under ice-cooling, and 2-anilinoethyl acetate hydrochloride (0.647 g) obtained in Reference Synthetic Example 27 was added thereto. A solution of triethylamine (0.419 mL) in tetrahydrofuran (1 mL) was added dropwise, and stirred at room temperature for 3 hrs. The reaction solution was concentrated under reduced pressure, and to the residue was added water (20 mL), and then extracted with ethyl acetate (50 mL). The ethyl acetate layer was washed with saturated brine (15 mL), and dried over anhydrous magnesium sulfate. The solution was concentrated under reduced pressure, and the residue was dissolved in tetrahydrofuran (10 mL). To the solution were added 5-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]sulfinyl]-1H-benzimidazole (0.829 g), triethylamine (0.669 mL) and 4-dimethylaminopyridine (0.012 g), and stirred at 60° C. for 14 hrs. The reaction solution was concentrated under reduced pressure, and to the residue was added water (40 mL), and extracted with ethyl acetate (80 mL). The ethyl acetate layer was washed with saturated brine (15 mL), and dried over anhydrous magnesium sulfate. After concentrating under reduced pressure, the residue was purified with basic silica gel column chromatography (eluted with ethyl acetate:hexane=1:2) to give a mixture of 1:1 of title compound and 2-[[[6-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]sulfinyl]-1H-benzimidazol-1-yl]carbonyl](phenyl)amino]ethyl acetate as colorless amorphous solid (1.10 g).

Workup

  1. additionwas added
  2. concentrationThe reaction solution was concentrated under reduced pressure
  3. additionto the residue was added water (20 mL)
  4. extractionextracted with ethyl acetate (50 mL)
  5. washThe ethyl acetate layer was washed with saturated brine (15 mL)
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationThe solution was concentrated under reduced pressure
  8. dissolutionthe residue was dissolved in tetrahydrofuran (10 mL)
  9. additionTo the solution were added 5-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]sulfinyl]-1H-benzimidazole (0.829 g), triethylamine (0.669 mL) and 4-dimethylaminopyridine (0.012 g)
  10. stirringstirred at 60° C. for 14 hrs
  11. concentrationThe reaction solution was concentrated under reduced pressure
  12. additionto the residue was added water (40 mL)
  13. extractionextracted with ethyl acetate (80 mL)
  14. washThe ethyl acetate layer was washed with saturated brine (15 mL)
  15. dry with materialdried over anhydrous magnesium sulfate
  16. concentrationAfter concentrating under reduced pressure
  17. customthe residue was purified with basic silica gel column chromatography (eluted with ethyl acetate:hexane=1:2)
  18. customto give

Sources & evidence

ORD record
ord-dd0501ea89184222b014aa524a466bb2
Source dataset
uspto-grants-2013_05
Patent number
US08449911B2

Reaction notes

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