Triethylamine → HCID 70157088, compound

HRID 1700354Notes

Reaction equation

HRID 1700354 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH:7]=[CH:8][CH2:9][NH2:10])=[CH:3][CH:2]=1.[Cl:11][C:12]1[CH:13]=[C:14]([CH:18]2[C:23]([C:24]([O-])=[O:25])=[C:22]([CH3:27])[NH:21][C:20]([CH3:28])=[C:19]2[C:29]([O:31][CH2:32][CH2:33][C:34]#[N:35])=[O:30])[CH:15]=[CH:16][CH:17]=1.Cl.CN(C)CCCN=C=NCC.C(N(CC)CC)C>CN(C=O)C>[Cl:11][C:12]1[CH:13]=[C:14]([CH:18]2[C:23]([C:24](=[O:25])[NH:10][CH2:9][CH:8]=[CH:7][C:4]3[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=3)=[C:22]([CH3:27])[NH:21][C:20]([CH3:28])=[C:19]2[C:29]([O:31][CH2:32][CH2:33][C:34]#[N:35])=[O:30])[CH:15]=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 54006116HCID 54006116, compoundHCID 86757801Mono(2-cyanoethyl) 4-(3-chlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate

Product 1

HCID 70157088HCID 70157088, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

221 mg (0.610 mmol) of 3-pyridine-4-yl-allylamine and 200 mg (0.554 mmol) of mono(2-cyanoethyl) 4-(3-chlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate were dissolved in 10 ml of DMF. 159 mg (0.831 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and 123 mg (1.22 mmol) of triethylamine were added to the obtained solution under cooling with ice, and they were stirred at room temperature for 2 days. DMF was evaporated under reduced pressure. After the extraction with a saturated aqueous sodium hydrogencarbonate solution and ethyl acetate, the organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue was purified by the silica gel chromatography (dichloromethane/methanol=100/1 to 10/1) to obtain the title compound.

Workup

  1. temperatureunder cooling with ice, and they
  2. customDMF was evaporated under reduced pressure
  3. extractionAfter the extraction with a saturated aqueous sodium hydrogencarbonate solution and ethyl acetate
  4. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by the silica gel chromatography (dichloromethane/methanol=100/1 to 10/1)

Sources & evidence

ORD record
ord-6e8a39b1a1054ac1b9847630343aa4c3
Source dataset
uspto-grants-2002_02
Patent number
US06350762B1

Reaction notes

Loading…