Boron trifluoride etherate → HCID 86635097, compound

HRID 1696254Notes

Reaction equation

HRID 1696254 reaction equation
[CH3:1][C@@H:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C@@H:3]1[N:8]1[C:12]2=[C:13]3[CH:19]=[CH:18][N:17](COCC[Si](C)(C)C)[C:14]3=[N:15][CH:16]=[C:11]2[N:10]([CH2:28][C:29]#[N:30])[C:9]1=[O:31].B(F)(F)F.CCOCC.C([O-])(=O)C.[Na+]>ClCCl>[CH3:1][C@@H:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C@@H:3]1[N:8]1[C:12]2=[C:13]3[CH:19]=[CH:18][NH:17][C:14]3=[N:15][CH:16]=[C:11]2[N:10]([CH2:28][C:29]#[N:30])[C:9]1=[O:31]

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 517045Sodium AcetateHCID 86635098HCID 86635098, compound

Product 1

HCID 86635097HCID 86635097, compoundYield 22.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of {1-[(1S,2R)-2-methylcyclohexyl]-2-oxo-6-{[2-(trimethylsilyl)ethoxy]methyl}-1,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridin-3(2H)-yl}acetonitrile (25 mg) in dichloromethane (1 mL) was added boron trifluoride etherate (35.7 μl) dropwise at 4° C. The mixture was stirred at ambient temperature for 0.5 hour. To the mixture was added 5.5M sodium acetate aqueous solution (0.207 mL) and the mixture was stirred at 80° C. for 4 hours. The mixture was extracted with chloroform and washed with water. The extract was dried over MgSO4, filtrated and concentrated under reduced pressure. The residue was purified by column chromatography on NH silica gel with EtOAc and n-hexane (50:50 to 95:5) to give {1-[(1S,2R)-2-methylcyclohexyl]-2-oxo-1,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridin-3(2H)-yl}acetonitrile (4 mg) as a white powder.

Workup

  1. stirringthe mixture was stirred at 80° C. for 4 hours
  2. extractionThe mixture was extracted with chloroform
  3. washwashed with water
  4. dry with materialThe extract was dried over MgSO4
  5. filtrationfiltrated
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography on NH silica gel with EtOAc and n-hexane (50:50 to 95:5)

Sources & evidence

ORD record
ord-b131c382c449483a8e706a1471d5dc47
Source dataset
uspto-grants-2012_04
Patent number
US08163767B2

Reaction notes

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