Piperidine → HCID 178518096, compound

HRID 916262Notes

Reaction equation

HRID 916262 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][C:22]([F:25])=[CH:21][C:20]=1[Cl:26])=O)C1C=CC=CC=1.[N:27]1[C:36]2[C:31](=[N:32][C:33]([CH:37]=O)=[CH:34][CH:35]=2)[CH:30]=[CH:29][CH:28]=1.N1CCCCC1>CC(O)C>[Cl:26][C:20]1[CH:21]=[C:22]([F:25])[CH:23]=[CH:24][C:19]=1[CH2:18][NH:17][C:12]1[NH:11][C:15](=[CH:37][C:33]2[CH:34]=[CH:35][C:36]3[C:31](=[CH:30][CH:29]=[CH:28][N:27]=3)[N:32]=2)[C:14](=[O:16])[N:13]=1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 115863361,5-Naphthyridine-2-carbaldehydeHCID 178516792HCID 178516792, compound

Product 1

HCID 178518096HCID 178518096, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a mixture of 2-(2-chloro-4-fluoro-benzylamino)-4-oxo-4,5-dihydro-imidazole-1-carboxylic acid benzyl ester (70.1 mg, 0.19 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 to give 2-(2-chloro-4-fluoro-benzylamino)-5-[1,5]naphthyridin-2-ylmethylene-1,5-dihydro-imidazol-4-one as a light yellow solid, 30.6 mg (43.0%). HR-ES (+) m/e calcd. for C19H13FClN5O: (M+H)+ 382.0866. Found: 382.0866.

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-5c0b90b89e014741ade219b7a92f58bc
Source dataset
uspto-grants-2007_09
Patent number
US07268231B2

Reaction notes

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