Triethylamine → HCID 19592330, compound

HRID 613525Notes

Reaction equation

HRID 613525 reaction equation
[Cl:1][C:2]1[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[C:3]=1[C:4]([NH:6][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:16]=1[N:15]=[CH:14][CH:13]=[C:12]2[N:17]([CH2:19][CH2:20][NH:21][CH3:22])[CH3:18])=[O:5].[N:28]1[CH:33]=[CH:32][CH:31]=[C:30]([C:34](Cl)=[O:35])[CH:29]=1.C(N(CC)CC)C>ClCCl>[Cl:1][C:2]1[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[C:3]=1[C:4]([NH:6][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:16]=1[N:15]=[CH:14][CH:13]=[C:12]2[N:17]([CH2:19][CH2:20][N:21]([CH3:22])[C:34]([C:30]1[CH:29]=[N:28][CH:33]=[CH:32][CH:31]=1)=[O:35])[CH3:18])=[O:5]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 82604Nicotinoyl chlorideHCID 19592623HCID 19592623, compound

Product 1

HCID 19592330HCID 19592330, compoundYield 91.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 8-(2,6-dichlorobenzoylamino)-4-[N-(2-methylaminoethyl)-N-methylamino]quinoline (130 mg), 3-pyridinecarbonyl chloride (60.3 mg) and triethylamine (97.9 mg) in dichloromethane (2 ml) was stirred at ambient temperature overnight. The mixture was diluted with dichloromethane, washed with water, dried over magnesium sulfate and evaporated in vacuo. The residue was crystallized from ethanol and collected by filtration. The residue was washed with ethanol to give 8-(2,6-dichlorobenzoylamino)-4-[N-[2-(N-methyl-3-pyridinecarboxamido)ethyl]-N-methylamino]quinoline (150 mg).

Workup

  1. washwashed with water
  2. dry with materialdried over magnesium sulfate
  3. customevaporated in vacuo
  4. customThe residue was crystallized from ethanol
  5. filtrationcollected by filtration
  6. washThe residue was washed with ethanol

Sources & evidence

ORD record
ord-056ed3bb2cc24537afc9095b49ed398a
Source dataset
uspto-grants-1999_12
Patent number
US06008230

Reaction notes

Loading…