Piperidine → HCID 178518207, compound

HRID 916260Notes

Reaction equation

HRID 916260 reaction equation
C(OC([N:11]1[CH2:15][C:14](=[O:16])[N:13]=[C:12]1[NH:17][C:18]([CH:20]1[CH2:22][CH2:21]1)=[O:19])=O)C1C=CC=CC=1.[N:23]1[C:32]2[C:27](=[N:28][C:29]([CH:33]=O)=[CH:30][CH:31]=2)[CH:26]=[CH:25][CH:24]=1.N1CCCCC1>CC(O)C>[N:28]1[C:27]2[C:32](=[N:23][CH:24]=[CH:25][CH:26]=2)[CH:31]=[CH:30][C:29]=1[CH:33]=[C:15]1[NH:11][C:12]([NH:17][C:18]([CH:20]2[CH2:21][CH2:22]2)=[O:19])=[N:13][C:14]1=[O:16]

Participants

5

Reactant 3

HCID 8082PiperidineHCID 115863361,5-Naphthyridine-2-carbaldehydeHCID 178516793HCID 178516793, compound

Product 1

HCID 178518207HCID 178518207, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a mixture of 2-(cyclopropanecarbonyl-amino)-4-oxo-4,5-dihydro-imidazole-1-carboxylic acid benzyl ester (109.6 mg, 0.36 mmol), 1,5-naphthyridine-6-carboxaldehyde (47.4 mg, 0.30 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 3.5 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 cyclopropanecarboxylic acid (5-[1,5]naphthyridin-2-ylmethylene-4-oxo-4,5-dihydro-1H-imidazol-2-yl)-amide as a light brown solid, 32.6 mg (35.4%). HR-ES (+) m/e calcd. for C16H13N5O2: (M)+ 307.1069. Found: 307.1066.

Workup

  1. temperaturethe suspension was then heated
  2. temperatureunder refluxing for 3.5 hrs
  3. customto give a suspension
  4. filtrationthe solid was collected by filtration
  5. washwashed with MeOH, and ether

Sources & evidence

ORD record
ord-e13cb76a41df4c41b93737fac32cca72
Source dataset
uspto-grants-2007_09
Patent number
US07268231B2

Reaction notes

Loading…