Piperidine → HCID 178474473, compound

HRID 916258Notes

Reaction equation

HRID 916258 reaction equation
C(OC([N:11]1[CH2:15][C:14](=[O:16])[N:13]=[C:12]1[NH:17][C:18](=[O:20])[CH3:19])=O)C1C=CC=CC=1.[N:21]1[C:30]2[C:25](=[N:26][C:27]([CH:31]=O)=[CH:28][CH:29]=2)[CH:24]=[CH:23][CH:22]=1.N1CCCCC1>CC(O)C>[N:26]1[C:25]2[C:30](=[N:21][CH:22]=[CH:23][CH:24]=2)[CH:29]=[CH:28][C:27]=1[CH:31]=[C:15]1[NH:11][C:12]([NH:17][C:18](=[O:20])[CH3:19])=[N:13][C:14]1=[O:16]

Participants

5

Reactant 3

HCID 8082PiperidineHCID 115863361,5-Naphthyridine-2-carbaldehydeHCID 694926452-Acetylamino-4-oxo-4,5-dihydro-imidazole-1-carboxylic acid benzyl ester

Product 1

HCID 178474473HCID 178474473, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a mixture of 2-acetylamino-4-oxo-4,5-dihydro-imidazole-1-carboxylic acid benzyl ester (47.1 mg, 0.17 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 N-(5-[1, 5]-naphthyridin-2-ylmethylene-4-oxo-4,5-dihydro-1H-imidazol-2-yl)-acetamide as a yellow solid, 15.3 mg (31.8%). HR-ES (+) m/e calcd. for C14H11N5O2: (M+H)+ 282.0986. Found: 282.0985.

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-7bcbc47082ed4dcab78e70146f66b10b
Source dataset
uspto-grants-2007_09
Patent number
US07268231B2

Reaction notes

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