Piperidine → HCID 178518085, compound

HRID 916264Notes

Reaction equation

HRID 916264 reaction equation
C(OC([N:11]1[CH2:15][C:14](=[O:16])[N:13]=[C:12]1[NH:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[C:25]([F:28])([F:27])[F:26])=O)C1C=CC=CC=1.[N:29]1[C:38]2[C:33](=[N:34][C:35]([CH:39]=O)=[CH:36][CH:37]=2)[CH:32]=[CH:31][CH:30]=1.N1CCCCC1>CC(O)C>[N:34]1[C:33]2[C:38](=[N:29][CH:30]=[CH:31][CH:32]=2)[CH:37]=[CH:36][C:35]=1[CH:39]=[C:15]1[NH:11][C:12]([NH:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[C:25]([F:26])([F:27])[F:28])=[N:13][C:14]1=[O:16]

Participants

5

Reactant 3

HCID 8082PiperidineHCID 115863361,5-Naphthyridine-2-carbaldehydeHCID 178516790benzyl 5-oxo-2-[[2-(trifluoromethyl)phenyl]methylamino]-4H-imidazole-3-carboxylate

Product 1

HCID 178518085HCID 178518085, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a mixture of 4-oxo-2-(2-trifluoromethyl-benzylamino)-4,5-dihydro-imidazole-1-carboxylic acid benzyl ester (70.4 mg, 0.18 mmol), 1,5-naphthyridine-6-carboxaldehyde (28.7 mg, 0.18 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. The solid was then re-crystallized from AcOEt-MeOH to give 5-[1,5]naphthyridin-2-ylmethylene-2-(2-trifluoromethybenzylamino)-1,5-dihydro-imidazol-4-one as a light yellow crystalline material (11.6 mg, 16.2%). HR-ES (+) m/e calcd. for C20H14F3N5O: (M+H)+ 398.1223. Found: 398.1222.

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
  6. customThe solid was then re-crystallized from AcOEt-MeOH

Sources & evidence

ORD record
ord-ccba878d3cbb44679ecf09e91ae5c515
Source dataset
uspto-grants-2007_09
Patent number
US07268231B2

Reaction notes

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