Piperidine → HCID 178518092, compound

HRID 916266Notes

Reaction equation

HRID 916266 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]([C:25]([F:28])([F:27])[F:26])=[CH:21][C:20]=1[C:29]([F:32])([F:31])[F:30])=O)C1C=CC=CC=1.[N:33]1[C:42]2[C:37](=[N:38][C:39]([CH:43]=O)=[CH:40][CH:41]=2)[CH:36]=[CH:35][CH:34]=1.N1CCCCC1>CC(O)C>[F:32][C:29]([F:30])([F:31])[C:20]1[CH:21]=[C:22]([C:25]([F:26])([F:28])[F:27])[CH:23]=[CH:24][C:19]=1[CH2:18][NH:17][C:12]1[NH:11][C:15](=[CH:43][C:39]2[CH:40]=[CH:41][C:42]3[C:37](=[CH:36][CH:35]=[CH:34][N:33]=3)[N:38]=2)[C:14](=[O:16])[N:13]=1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 115863361,5-Naphthyridine-2-carbaldehydeHCID 178516791benzyl 2-[[2,4-bis(trifluoromethyl)phenyl]methylamino]-5-oxo-4H-imidazole-3-carboxylate

Product 1

HCID 178518092HCID 178518092, compoundYield 23.2%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a mixture of 2-(2,4-bis-trifluoromethyl-benzylamino)-4-oxo-4,5-dihydro-imidazole-1-carboxylic acid benzyl ester (94.5 mg, 0.20 mmol), 1,5-naphthyridine-6-carboxaldehyde (31.7 mg, 0.20 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 4.5 hrs to give a suspension. The reaction mixture was cooled to r.t. and the solid was collected by filtration, washed with MeOH, ether and dried in vacuum at 100° C. for 3 h to give 2-(2,4-bis-trifluoromethyl-benzylamino)-5-[1,5]naphthyridin-2-ylmethylene-1,5-dihydro-imidazol-4-one as a light yellow solid (21.6 mg, 23.2%). HR-ES (+) m/e calcd. for C21H13F6N5O: (M+H)+ 466.1097. Found: 466.1098.

Workup

  1. temperaturethe suspension was then heated
  2. temperatureunder refluxing for 4.5 hrs
  3. customto give a suspension
  4. filtrationthe solid was collected by filtration
  5. washwashed with MeOH, ether
  6. customdried in vacuum at 100° C. for 3 h

Sources & evidence

ORD record
ord-874b71edcef0406c927ba1bdd70c33d4
Source dataset
uspto-grants-2007_09
Patent number
US07268231B2

Reaction notes

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