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Sodium Iodide → 4,5-Dihydro-4-[2-(1-tert-butoxycarbonylpiperidin-4-yl)ethan-1-yl]-3H-1,4,8b-triazaacenaphthylen-3-one

HRID 1068778
Notes
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Reaction equation

HRID 1068778 reaction equation
S(O)(O)(=O)=O.[C:6]([C:11]1[N:15]2[C:16]([CH2:20]Cl)=[CH:17][CH:18]=[CH:19][C:14]2=[N:13][CH:12]=1)([O:8]CC)=O.C1CCN2C(=NCCC2)CC1.[C:33]([O:37][C:38]([N:40]1[CH2:45][CH2:44][CH:43]([CH2:46][CH2:47][NH2:48])[CH2:42][CH2:41]1)=[O:39])([CH3:36])([CH3:35])[CH3:34].[I-].[Na+]>C(#N)C.C(N(CC)CC)C>[C:33]([O:37][C:38]([N:40]1[CH2:45][CH2:44][CH:43]([CH2:46][CH2:47][N:48]2[CH2:20][C:16]3[N:15]4[C:11](=[CH:12][N:13]=[C:14]4[CH:19]=[CH:18][CH:17]=3)[C:6]2=[O:8])[CH2:42][CH2:41]1)=[O:39])([CH3:36])([CH3:35])[CH3:34]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 1514258tert-Butyl 4-(2-aminoethyl)piperidine-1-carboxylateHCID 702111023-Carbethoxy-5-chloromethylimidazo[1,2-a]pyridine sulfate

Product 1

HCID 211902154,5-Dihydro-4-[2-(1-tert-butoxycarbonylpiperidin-4-yl)ethan-1-yl]-3H-1,4,8b-triazaacenaphthylen-3-one
Yield 37.5%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8471TriethylamineSolvent

Procedure

In 50 ml of acetonitrile was suspended 6.73 g (20.0 mM) of 3-carbethoxy-5-chloromethylimidazo[1,2-a]pyridine sulfate followed by addition of 5.97 ml (40.0 mM) of DBU at room temperature with stirring. To the resulting solution was added 4.57 g (20.0 mM) of 2-(1-tert-butoxycarbonylpiperidin-4-yl)-1-ethylamine as well as 5.54 ml (40.0 mM) of triethylamine and 3.00 g (20.0 mM) of sodium iodide and the mixture was stirred at room temperature for 16 hours. After completion of the reaction, the solvent was distilled off under reduced pressure and the residue was extracted with 100 ml of 2-butanone. The organic layer was washed with 100 ml of saturated aqueous NaCl solution and dried over MgSO4 and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (eluent: ethyl acetate-ethanol=5:1) to provide 2.88 g (yield 37.5%) of the title compound as yellow oil.

Workup

  1. stirringthe mixture was stirred at room temperature for 16 hours
  2. customAfter completion of the reaction
  3. distillationthe solvent was distilled off under reduced pressure
  4. extractionthe residue was extracted with 100 ml of 2-butanone
  5. washThe organic layer was washed with 100 ml of saturated aqueous NaCl solution
  6. dry with materialdried over MgSO4
  7. distillationthe solvent was distilled off under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (eluent: ethyl acetate-ethanol=5:1)

Sources & evidence

ORD record
ord-454fced77a1942c690cc5d19ba0623e2
Source dataset
uspto-grants-2001_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06251905B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes