Triethylamine → HCID 85050797, compound

HRID 1700334Notes

Reaction equation

HRID 1700334 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]2[C:13]([N+:14]([O-:16])=[O:15])=[C:12]([CH3:17])[NH:11][C:10]([CH3:18])=[C:9]2[C:19](O)=[O:20])[CH:5]=[CH:6][CH:7]=1.[CH2:22]([NH2:31])[CH:23]=[CH:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.[I-].ClC1C=CC=C[N+]=1C.C(N(CC)CC)C>CN(C=O)C>[C:25]1([CH:24]=[CH:23][CH2:22][NH:31][C:19]([C:9]2[CH:8]([C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=3)[C:13]([N+:14]([O-:16])=[O:15])=[C:12]([CH3:17])[NH:11][C:10]=2[CH3:18])=[O:20])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 203693-Phenylprop-2-en-1-amineHCID 1670692-Chloro-1-methylpyridinium iodideHCID 18318293HCID 18318293, compound

Product 1

HCID 85050797HCID 85050797, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

93 mg (0.30 mmol) of 4-(3-chlorophenyl)-2,6-dimethyl-5-nitro-1,4-dihydropyridine-3-carboxylic acid, 100 mg (0.75 mmol) of cinnamylamine, 138 mg (0.54 mmol) of 2-chloro-1-methylpyridinium iodide and 0.15 ml (1.08 mmol) of triethylamine were stirred in 5 ml of DMF at room temperature for 2 days. DMF was evaporated under reduced pressure. Ethyl acetate was added to the reaction mixture. After washing with 1 N hydrochloric acid, the organic layer was dried over anhydrous sodium sulfate. After the concentration under reduced pressure, the residue was purified by the silica gel chromatography (hexane/ethyl cetate=4/1) to obtain the title compound.

Workup

  1. customDMF was evaporated under reduced pressure
  2. additionEthyl acetate was added to the reaction mixture
  3. washAfter washing with 1 N hydrochloric acid
  4. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  5. concentrationAfter the concentration under reduced pressure
  6. customthe residue was purified by the silica gel chromatography (hexane/ethyl cetate=4/1)

Sources & evidence

ORD record
ord-69cdb4515086431aa9e8d8034c187346
Source dataset
uspto-grants-2002_02
Patent number
US06350762B1

Reaction notes

Loading…