Piperidine → HCID 178453000, compound

HRID 916256Notes

Reaction equation

HRID 916256 reaction equation
C(OC([N:11]1[CH2:15][C:14](=[O:16])[N:13]=[C:12]1[NH:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=O)C1C=CC=CC=1.[N:25]1[C:34]2[C:29](=[N:30][C:31]([CH:35]=O)=[CH:32][CH:33]=2)[CH:28]=[CH:27][CH:26]=1.N1CCCCC1>CC(O)C>[C:21]([O:20][C:18](=[O:19])[NH:17][C:12]1[NH:11][C:15](=[CH:35][C:31]2[CH:32]=[CH:33][C:34]3[C:29](=[CH:28][CH:27]=[CH:26][N:25]=3)[N:30]=2)[C:14](=[O:16])[N:13]=1)([CH3:22])([CH3:23])[CH3:24]

Participants

5

Reactant 3

HCID 8082PiperidineHCID 115863361,5-Naphthyridine-2-carbaldehydeHCID 178453002HCID 178453002, compound

Product 1

HCID 178453000HCID 178453000, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a mixture of 2-tert-butoxycarbonylamino-4-oxo-4,5-dihydro-imidazole-1-carboxylic acid benzyl ester (53.3 mg, 0.16 mmol), 1,5-naphthyridine-6-carboxaldehyde (31.6 mg, 0.2 mmol) and iPrOH (5.0 mL) in a 25-mL round bottom flask was added piperidine (0.05 mL) and the suspension was then heated under refluxing for 3 hrs to give a suspension. The reaction mixture was cooled to r.t. and the solid was collected by filtration to give (5-[1,5]-naphthyridin-2-ylmethylene-4-oxo-4,5-dihydro-1H-imidazol-2-yl)-carbamic acid tert-butyl ester as a yellow solid, 29.8 mg (54.9%). HR-ES (+) m/e calcd. for C17H17N5O3: (M+H)+ 340.1404. Found: 340.1404.

Workup

  1. temperaturethe suspension was then heated
  2. temperatureunder refluxing for 3 hrs
  3. customto give a suspension
  4. filtrationthe solid was collected by filtration

Sources & evidence

ORD record
ord-ec6fdc4ecaab414b9e522a8478a6e131
Source dataset
uspto-grants-2007_09
Patent number
US07268231B2

Reaction notes

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