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Piperidine → N-(4-tert-butylbenzyl)-2,5-dimethyl-1,8-naphthyridine-3-carboxamide

HRID 1961472
Notes
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Reaction equation

HRID 1961472 reaction equation
[C:1]([C:5]1[CH:18]=[CH:17][C:8]([CH2:9][NH:10][C:11](=[O:16])[CH2:12][C:13](=O)[CH3:14])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[NH2:19][C:20]1[N:27]=[CH:26][CH:25]=[C:24]([CH3:28])[C:21]=1[CH:22]=O.N1CCCCC1.CCOC(C)=O>CCO>[C:1]([C:5]1[CH:18]=[CH:17][C:8]([CH2:9][NH:10][C:11]([C:12]2[C:13]([CH3:14])=[N:19][C:20]3[C:21]([CH:22]=2)=[C:24]([CH3:28])[CH:25]=[CH:26][N:27]=3)=[O:16])=[CH:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8082PiperidineHCID 8857Ethyl AcetateHCID 641277472-Amino-4-methylpyridine-3-carbaldehydeHCID 86661979N-(4-tert-butylbenzyl)-3-oxobutanamide

Product 1

HCID 66632776N-(4-tert-butylbenzyl)-2,5-dimethyl-1,8-naphthyridine-3-carboxamide

Reagents, catalysts & solvents 1

HCID 702
Ethanol
Solvent

Conditions

Temperature
120 °C

Procedure

In a screw cap pressure tube were N-(4-tert-butylbenzyl)-3-oxobutanamide (94.5 mg, 0.38 mmol), 2-amino-4-methylnicotinaldehyde (52.0 mg, 0.38 mmol) and piperidine (151.0 μl, 1.53 mmol) suspended in EtOH (0.5 ml). The tube was sealed and the mixture heated to 120° C. for 1.5 h. The mixture was allowed to cool. EtOAc was added and the mixture washed with H2O, dried (MgSO4), filtered and concentrated. The crude product was purified by flash chromatography CH2Cl2/MeOH 96/4 yielding 61.5 mg of the title compound (47%).

Workup

  1. customIn a screw cap pressure tube
  2. customThe tube was sealed
  3. temperatureto cool
  4. washthe mixture washed with H2O
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product was purified by flash chromatography CH2Cl2/MeOH 96/4 yielding 61.5 mg of the title compound (47%)

Sources & evidence

ORD record
ord-6b9578044c0f45c8889ce1379e8dafb6
Source dataset
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08415333B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes