Triethylamine → HCID 69837392, compound

HRID 2415131Notes

Reaction equation

HRID 2415131 reaction equation
[CH3:1][N:2]([CH3:16])[C:3]([C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]=[C:7]([Cl:15])[CH:6]=1)=[O:4].[NH2:17][CH2:18][CH2:19][CH2:20][NH:21]C(=O)OC(C)(C)C.C(N(CC)CC)C>C(O)C>[ClH:15].[ClH:15].[CH3:1][N:2]([CH3:16])[C:3]([C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]=[C:7]([NH:17][CH2:18][CH2:19][CH2:20][NH2:21])[CH:6]=1)=[O:4]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2735700tert-Butyl (3-aminopropyl)carbamateHCID 430827022-chloro-N,N-dimethylquinoline-4-carboxamide

Product 1

HCID 69837392HCID 69837392, compoundYield 57.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-chloroquinoline-4-carboxylic acid dimethylamide (512 mg, 2.18 mmol), tert-butyl N-(3-aminopropyl)carbamate (571 μl, 3.27 mmol), and triethylamine (608 μl, 4.36 mmol) in absolute ethanol (35 ml) was heated at reflux for 7 days. The reaction was then allowed to cool to ambient temperature and was evaporated under reduced pressure to give a yellow oil. The residue was purified by column chromatography (ethyl acetate), dissolved in methylene chloride (10 mL), and treated with 4 N hydrogen chloride in dioxane (3 mL). The reaction was maintained at ambient temperature for 24 hours. Evaporation under reduced pressure gave 2-(3-aminopropylamino)quinoline-4-carboxylic acid dimethylamide dihydrochloride (218 mg, 30%) as a pale yellow solid. [M+H]+ 273.

Workup

  1. temperatureat reflux for 7 days
  2. customwas evaporated under reduced pressure
  3. customto give a yellow oil
  4. customThe residue was purified by column chromatography (ethyl acetate)
  5. dissolutiondissolved in methylene chloride (10 mL)
  6. additiontreated with 4 N hydrogen chloride in dioxane (3 mL)
  7. temperatureThe reaction was maintained at ambient temperature for 24 hours
  8. customEvaporation under reduced pressure

Sources & evidence

ORD record
ord-cb58942ae3db4043becf78a5d21c0671
Source dataset
uspto-grants-2004_11
Patent number
US06818655B2

Reaction notes

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