1-Benzyl-1,2-dihydropyridine-4-carboxamide → HCID 18634675, compound

HRID 1494178Notes

Reaction equation

HRID 1494178 reaction equation
[I-].[I-].[CH3:3][N+:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]([O:12][C:13]2[CH:30]=[CH:29][C:28]3[C@@H:27]4[C@H:18]([C@H:19]5[C@@:23]([CH2:25][CH2:26]4)([CH3:24])[C@@H:22]([O:31][C:32]([C:34]4[CH:35]=[N+:36]([CH3:40])[CH:37]=[CH:38][CH:39]=4)=[O:33])[CH2:21][CH2:20]5)[CH2:17][CH2:16][C:15]=3[CH:14]=2)=[O:11])[CH:5]=1.C1(CN2C=CC(C(N)=O)=CC2)C=CC=CC=1>C(#N)C.C(Cl)Cl>[CH3:3][N:4]1[CH:9]=[CH:8][CH2:7][C:6]([C:10]([O:12][C:13]2[CH:30]=[CH:29][C:28]3[C@@H:27]4[C@H:18]([C@H:19]5[C@@:23]([CH2:25][CH2:26]4)([CH3:24])[C@@H:22]([O:31][C:32]([C:34]4[CH2:39][CH:38]=[CH:37][N:36]([CH3:40])[CH:35]=4)=[O:33])[CH2:21][CH2:20]5)[CH2:17][CH2:16][C:15]=3[CH:14]=2)=[O:11])=[CH:5]1

Participants

5

Reactant 2

HCID 132279601-Benzyl-1,2-dihydropyridine-4-carboxamideHCID 13731100HCID 13731100, compound

Product 1

HCID 18634675HCID 18634675, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

One gram (1.31 mmol) of the product of Example 71 was dissolved in 100 mL of dry acetonitrile. To that solution, which was flushed with nitrogen, 0.28 g (1.31 mmol) of 1-(phenylmethyl)-4-(aminocarbonyl)-1,2-dihydropyridine was added, and the reaction mixture was stirred at 0° C. for 1 hour. Removal of the solvent under reduced pressure afforded a solid, which was suspended in methylene chloride and removed by filtration. The filtrate was chromatographed several times on a neutral alumina column prepared with methylene chloride. Purification and evaporation of the solvent in vacuo gave a solid foam. The product had the formula ##STR105## as confirmed by UV, NMR and elemental analyses.

Workup

  1. additionwas added
  2. customRemoval of the solvent under reduced pressure
  3. customafforded a solid, which
  4. customremoved by filtration
  5. customThe filtrate was chromatographed several times on a neutral alumina column
  6. customprepared with methylene chloride
  7. customPurification and evaporation of the solvent in vacuo
  8. customgave a solid foam

Sources & evidence

ORD record
ord-8fd0664f951941a3b1113e312c605cee
Source dataset
uspto-grants-1991_06
Patent number
US05024998

Reaction notes

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