Triethylamine → HCID 19592523, compound

HRID 613524Notes

Reaction equation

HRID 613524 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]([NH:34][C:35](=[O:43])OC2C=CC=CC=2)[CH:29]=1.C(N(CC)CC)C>CN(C)C=O.C(OCC)(=O)C>[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:35]([NH:34][C:30]1[CH:29]=[N:28][CH:33]=[CH:32][CH:31]=1)=[O:43])[CH3:18])=[O:5]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 6935890Phenyl pyridin-3-ylcarbamateHCID 19592623HCID 19592623, compound

Product 1

HCID 19592523HCID 19592523, compoundYield 99.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 8-(2,6-dichlorobenzoylamino)-4-[N-(2-methylaminoethyl)-N-methylamino]quinoline (130 mg), phenyl 3-pyridylcarbamate (76 mg) and triethylamine (97.9 mg) in dimethylformamide (1.5 ml) was stirred for 1 hour at ambient temperature. The mixture was diluted with ethyl acetate, washed with 1N sodium hydroxide solution, water and brine, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by preparative thin layer chromatography (methanol-dichloromethane) to give 8-(2,6-dichlorobenzoylamino)-4-[N-[2-[l-methyl-3-(3-pyridyl)ureido)ethyl]-N-methylamino]quinoline (168 mg).

Workup

  1. washwashed with 1N sodium hydroxide solution, water and brine
  2. dry with materialdried over magnesium sulfate
  3. customevaporated in vacuo
  4. customThe residue was purified by preparative thin layer chromatography (methanol-dichloromethane)

Sources & evidence

ORD record
ord-ff050f340483401e8957f112bb528c59
Source dataset
uspto-grants-1999_12
Patent number
US06008230

Reaction notes

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