Triethylamine → HCID 59311439, compound

HRID 1693268Notes

Reaction equation

HRID 1693268 reaction equation
C[Si]([C:5]#[N:6])(C)C.C(N(CC)CC)C.[Cl:14][C:15]1[N:20]=[C:19]([N:21]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[N:18]=[C:17]2[N:36]([CH2:42][C:43]3[C:48]([CH3:49])=[C:47]([O:50][CH3:51])[C:46]([CH3:52])=[CH:45][N:44]=3)[N:37]=[C:38]([CH2:39][CH:40]=[O:41])[C:16]=12>ClCCl>[Cl:14][C:15]1[N:20]=[C:19]([N:21]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[C:22]([O:24][C:25]([CH3:26])([CH3:28])[CH3:27])=[O:23])[N:18]=[C:17]2[N:36]([CH2:42][C:43]3[C:48]([CH3:49])=[C:47]([O:50][CH3:51])[C:46]([CH3:52])=[CH:45][N:44]=3)[N:37]=[C:38]([CH2:39][CH:40]([C:5]#[N:6])[OH:41])[C:16]=12

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 82115Trimethylsilyl cyanideHCID 59311456HCID 59311456, compound

Product 1

HCID 59311439HCID 59311439, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trimethylsilyl cyanide (0.219 mL) and triethylamine (0.198 mL) were added to a mixture composed of the above di-tert-butyl {4-chloro-1-[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]-3-(2-oxoethyl)-1H-pyrazolo[3,4-d]pyrimidin-6-yl}imidodicarbonate (796 mg) and dichloromethane (10 mL) under cooling in an ice bath. Then, the ice bath was removed and the mixture was stirred for 16 hours. Chloroform (80 mL) and a 0.5 N hydrochloric acid solution (100 mL) were added to the reaction mixture, followed by separation. The organic layer was dried over anhydrous magnesium sulfate and filtered. Then, the filtrate was concentrated under reduced pressure. The resulting residue was dissolved in acetonitrile (20 mL). A 1 N hydrochloric acid solution (10 mL) was added and the mixture was stirred at room temperature for 30 minutes. A saturated sodium bicarbonate solution (80 mL) was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate and then filtered. The filtrate was concentrated under reduced pressure and the solvent was evaporated to obtain a crude product of the title compound (788 mg, 94%). The resulting compound was directly used for the next reaction without purification.

Workup

  1. temperatureunder cooling in an ice bath
  2. customThen, the ice bath was removed
  3. additionChloroform (80 mL) and a 0.5 N hydrochloric acid solution (100 mL) were added to the reaction mixture
  4. customfollowed by separation
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationThen, the filtrate was concentrated under reduced pressure
  8. dissolutionThe resulting residue was dissolved in acetonitrile (20 mL)
  9. additionA 1 N hydrochloric acid solution (10 mL) was added
  10. stirringthe mixture was stirred at room temperature for 30 minutes
  11. additionA saturated sodium bicarbonate solution (80 mL) was added to the reaction mixture
  12. extractionfollowed by extraction with ethyl acetate
  13. washThe organic layer was washed with brine
  14. dry with materialdried over anhydrous sodium sulfate
  15. filtrationfiltered
  16. concentrationThe filtrate was concentrated under reduced pressure
  17. customthe solvent was evaporated

Sources & evidence

ORD record
ord-78ddac608bb2416d9d811e5c60987d62
Source dataset
uspto-grants-2012_04
Patent number
US08158638B2

Reaction notes

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