Piperidine → HCID 178429652, compound

HRID 916267Notes

Reaction equation

HRID 916267 reaction equation
C(OC([N:11]1[CH2:15][C:14](=[O:16])[N:13]=[C:12]1[NH:17][C:18]([C:20]1[S:21][CH:22]=[CH:23][C:24]=1[CH3:25])=[O:19])=O)C1C=CC=CC=1.[N:26]1[C:35]2[C:30](=[N:31][C:32]([CH:36]=O)=[CH:33][CH:34]=2)[CH:29]=[CH:28][CH:27]=1.N1CCCCC1>CC(O)C>[N:31]1[C:30]2[C:35](=[N:26][CH:27]=[CH:28][CH:29]=2)[CH:34]=[CH:33][C:32]=1[CH:36]=[C:15]1[NH:11][C:12]([NH:17][C:18]([C:20]2[S:21][CH:22]=[CH:23][C:24]=2[CH3:25])=[O:19])=[N:13][C:14]1=[O:16]

Participants

5

Reactant 3

HCID 8082PiperidineHCID 115863361,5-Naphthyridine-2-carbaldehydeHCID 178429653HCID 178429653, compound

Product 1

HCID 178429652HCID 178429652, compoundYield 30.5%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a mixture of 2-[(3-methyl-thiophene-2-carbonyl)-amino]-4-oxo-4,5-dihydro-imidazole-1-carboxylic acid benzyl ester (42.0 mg, 0.12 mmol), 1,5-naphthyridine-6-carboxaldehyde (18.6 mg, 0.12 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 4 hrs to give a suspension. The reaction mixture was cooled to r.t. and the solid was collected by filtration, washed with MeOH, and ether to give 3-methyl-thiophene-2-carboxylic acid (5-[1,5]naphthyridin-2-ylmethylene-4-oxo-4,5-dihydro-1H-imidazol-2-yl)-amide as a light yellow solid (13.3 mg, 30.5%). HR-ES (+) m/e calcd. for C18H13N5O2S: (M+H)+ 364.0863. Found: 364.0862.

Workup

  1. temperaturethe suspension was then heated
  2. temperatureunder refluxing for 4 hrs
  3. customto give a suspension
  4. filtrationthe solid was collected by filtration
  5. washwashed with MeOH, and ether

Sources & evidence

ORD record
ord-1e1cc1851098406483648bd5690e7ad4
Source dataset
uspto-grants-2007_09
Patent number
US07268231B2

Reaction notes

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