Hydrochloric Acid → HCID 67277919, compound

HRID 1696243Notes

Reaction equation

HRID 1696243 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]2[CH:36]=[CH:35][C:32]([C:33]#[N:34])=[CH:31][CH:30]=2)[C:9]1=[O:37].Cl>O1CCOCC1>[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]2[CH:30]=[CH:31][C:32]([C:33]#[N:34])=[CH:35][CH:36]=2)[C:9]1=[O:37]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67278103HCID 67278103, compound

Product 1

HCID 67277919HCID 67277919, compoundYield 96.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of rel-4-({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}methyl)benzonitrile (50 mg) in dioxane (0.5 mL) was added 4M hydrogen chloride in dioxane (1 mL) and the mixture was stirred at ambient temperature for 1 hour. The mixture was concentrated under reduced pressure and the residue was extracted with chloroform. The extract was washed with saturated sodium hydrogencarbonate aqueous solution and brine, dried over MgSO4, filtrated and concentrated under reduced pressure. The residue was dissolved in tetrahydrofuran (1 mL). To the mixture were added 1M NaOH solution (0.29 mL) and 1,2-ethanediamine (0.2 mL). The mixture was stirred at ambient temperature for 2 hours. The mixture was extracted with chloroform. The extract was washed with water, dried over MgSO4, filtrated and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel with chloroform and methanol (100:0 to 90:10) to give rel-4-({1-[(1S,2R)-2-methylcyclohexyl]-2-oxo-1,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridin-3(2H)-yl}methyl)benzonitrile (36 mg) as a white powder.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. extractionthe residue was extracted with chloroform
  3. washThe extract was washed with saturated sodium hydrogencarbonate aqueous solution and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltrated
  6. concentrationconcentrated under reduced pressure
  7. dissolutionThe residue was dissolved in tetrahydrofuran (1 mL)
  8. additionTo the mixture were added 1M NaOH solution (0.29 mL) and 1,2-ethanediamine (0.2 mL)
  9. stirringThe mixture was stirred at ambient temperature for 2 hours
  10. extractionThe mixture was extracted with chloroform
  11. washThe extract was washed with water
  12. dry with materialdried over MgSO4
  13. filtrationfiltrated
  14. concentrationconcentrated under reduced pressure
  15. customThe residue was purified by column chromatography on silica gel with chloroform and methanol (100:0 to 90:10)

Sources & evidence

ORD record
ord-ff51196a1612425781a31a252d354aa5
Source dataset
uspto-grants-2012_04
Patent number
US08163767B2

Reaction notes

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