Triethylamine → 4-[3-(3-Quinolineacryloylamino)propylthio]pyridine

HRID 6115Notes

Reaction equation

HRID 6115 reaction equation
Cl.Cl.[NH2:3][CH2:4][CH2:5][CH2:6][S:7][C:8]1[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=1.C(N(CC)CC)C.[N:21]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:24]=[C:23]([CH:31]=[CH:32][C:33](Cl)=[O:34])[CH:22]=1>C(Cl)Cl>[N:21]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:24]=[C:23]([CH:31]=[CH:32][C:33]([NH:3][CH2:4][CH2:5][CH2:6][S:7][C:8]2[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=2)=[O:34])[CH:22]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 190792594-(3-Aminopropylthio)pyridine dihydrochlorideHCID 540190183-Quinolineacryloyl chloride

Product 1

HCID 677397574-[3-(3-Quinolineacryloylamino)propylthio]pyridineYield 83.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 396 mg (1.64 mmol) of 4-(3-aminopropylthio)pyridine dihydrochloride and 0.27 ml (1.97 mmol) of triethylamine in 20 ml of methylene chloride, 500 mg (1.96 mmol) of 3-quinolineacryloyl chloride hydrochlride was added under ice-cooling with stirring. The mixture was stirred at room temperature for 30 minutes. The reaction mixture was washed with a saturated aqueous solution of sodium bicarbonate and water and dried, and then the solvent was distilled off. The residue was purified by column chromatography (eluent: methanol/ethyl acetate=1:10) to obtain powder. The powder was washed with ether and dried to obtain the desired compound (480 mg, yield: 83.8%, pale yellow powder).

Workup

  1. temperaturecooling
  2. stirringThe mixture was stirred at room temperature for 30 minutes
  3. washThe reaction mixture was washed with a saturated aqueous solution of sodium bicarbonate and water
  4. customdried
  5. distillationthe solvent was distilled off
  6. customThe residue was purified by column chromatography (eluent: methanol/ethyl acetate=1:10)
  7. customto obtain powder
  8. washThe powder was washed with ether
  9. customdried

Sources & evidence

ORD record
ord-a551cb2a1c7144368de100ddce8580d5
Source dataset
uspto-grants-1993_09
Patent number
US05246948

Reaction notes

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