1-Hydroxybenzotriazole → HCID 67103523, compound

HRID 2080900Notes

Reaction equation

HRID 2080900 reaction equation
[CH2:1]([N:4]([CH2:29][CH2:30][CH3:31])[CH2:5][CH2:6][CH2:7][CH2:8][N:9]([CH2:11][C:12]1[CH:20]=[CH:19][C:18]([CH2:21][O:22]CC(OC)OC)=[CH:17][C:13]=1[C:14]([OH:16])=[O:15])[CH3:10])[CH2:2][CH3:3].[CH3:32]CN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1>C(O)C>[CH3:32][O:16][C:14](=[O:15])[C:13]1[CH:17]=[C:18]([CH2:21][OH:22])[CH:19]=[CH:20][C:12]=1[CH2:11][N:9]([CH2:8][CH2:7][CH2:6][CH2:5][N:4]([CH2:29][CH2:30][CH3:31])[CH2:1][CH2:2][CH3:3])[CH3:10]

Participants

5

Reactant 3

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 67103629HCID 67103629, compound

Product 1

HCID 67103523HCID 67103523, compoundYield 38.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The compound (263.3 mg) obtained in Example 102-3 was dissolved in ethanol (6 ml). The reaction solution was added with WSCI hydrochloride (147.5 mg) and HOBt (104.9 mg) and the whole was stirred at room temperature for 4 hours. The reaction solution was concentrated under reduced pressure and added with a 1 mol/l sodium hydroxide aqueous solution, followed by extraction with chloroform. The organic layer was washed with a saturated saline solution and dried with anhydrous sodium sulfate. After the drying agent was filtrated out, the filtrate was concentrated under reduced pressure. The resultant residue was dissolved in 2-methyl-2-propanol (6 ml). The reaction solution was added with pyridinium p-toluenesulfonate (35.2 mg) and the whole was refluxed under heating for 2 days. After that, the solution was added with 1 mol/l hydrochloric acid (4 ml) and stirred at 90° C. for 30 minutes. After having been cooled to room temperature, the reaction solution was subjected to extraction with chloroform. The aqueous layer was added with a 1 mol/l sodium hydroxide aqueous solution to thereby adjust to pH 13, followed by extraction with chloroform. The organic layer was washed with a saturated saline solution and dried with anhydrous sodium sulfate. After the drying agent was filtrated out, the filtrate was concentrated under reduced pressure. The resultant residue was purified through silica gel column chromatography (hexane/ethyl acetate) thereby obtaining the subject compound (83.5 mg) as a colorless oily substance.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. additionadded with a 1 mol/l sodium hydroxide aqueous solution
  3. extractionfollowed by extraction with chloroform
  4. washThe organic layer was washed with a saturated saline solution
  5. dry with materialdried with anhydrous sodium sulfate
  6. filtrationAfter the drying agent was filtrated out
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. dissolutionThe resultant residue was dissolved in 2-methyl-2-propanol (6 ml)
  9. additionThe reaction solution was added with pyridinium p-toluenesulfonate (35.2 mg)
  10. temperaturethe whole was refluxed
  11. temperatureunder heating for 2 days
  12. additionAfter that, the solution was added with 1 mol/l hydrochloric acid (4 ml)
  13. stirringstirred at 90° C. for 30 minutes
  14. temperatureAfter having been cooled to room temperature
  15. extractionthe reaction solution was subjected to extraction with chloroform
  16. additionThe aqueous layer was added with a 1 mol/l sodium hydroxide aqueous solution
  17. extractionfollowed by extraction with chloroform
  18. washThe organic layer was washed with a saturated saline solution
  19. dry with materialdried with anhydrous sodium sulfate
  20. filtrationAfter the drying agent was filtrated out
  21. concentrationthe filtrate was concentrated under reduced pressure
  22. customThe resultant residue was purified through silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-df57290494b049c49f37221d0e28a5a0
Source dataset
uspto-grants-2011_04
Patent number
US07932281B2

Reaction notes

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