Dimethylformamide → N-methoxy-N-methyl-5-(2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)pentanamide

HRID 521332Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 521332
C(Cl)(=O)C(Cl)=O.[CH2:7]([C:10]1[N:11]([CH2:23][CH2:24][CH2:25][CH2:26][C:27]([OH:29])=O)[C:12]2[C:21]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[N:15]=[CH:14][C:13]=2[N:22]=1)[CH2:8][CH3:9].Cl.[CH3:31][NH:32][O:33][CH3:34].CN(C)C=O>ClCCl>[CH3:34][O:33][N:32]([CH3:31])[C:27](=[O:29])[CH2:26][CH2:25][CH2:24][CH2:23][N:11]1[C:12]2[C:21]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[N:15]=[CH:14][C:13]=2[N:22]=[C:10]1[CH2:7][CH2:8][CH3:9]

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 574470705-(2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)pentanoic acid

Produkt 1

HCID 86611639N-methoxy-N-methyl-5-(2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)pentanamideAusbeute 92,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Oxalyl chloride (2.62 mL, 30.1 mmol) was added to a solution of 5-(2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)pentanoic acid (5.21 g, 16.7 mmol) in dichloromethane (50 mL) at room temperature. The reaction was stirred for 1 hour, then the volatiles were removed under reduced pressure. Dichloromethane (50 mL) was added to the residue, followed by N,O-dimethylhydroxylamine hydrochloride (3.26 g, 33.5 mmol) and N,N-dimethylformamide (2 mL). The reaction mixture was stirred at room temperature overnight, then was concentrated under reduced pressure. The residue was diluted with dichloromethane and an ammonium hydroxide solution. The mixture was transferred to a separatory funnel and the layers were separated. The organic layer was washed with saturated aqueous sodium bicarbonate and brine, dried over magnesium sulfate, filtered, and concentrated under reduced pressure to afford 5.5 g of crude N-methoxy-N-methyl-5-(2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)pentanamide as a brown oil that was used without purification in the next step.

Aufarbeitung

  1. customthe volatiles were removed under reduced pressure
  2. additionDichloromethane (50 mL) was added to the residue
  3. stirringThe reaction mixture was stirred at room temperature overnight
  4. concentrationwas concentrated under reduced pressure
  5. additionThe residue was diluted with dichloromethane
  6. customThe mixture was transferred to a separatory funnel
  7. customthe layers were separated
  8. washThe organic layer was washed with saturated aqueous sodium bicarbonate and brine
  9. dry with materialdried over magnesium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-c1d2e08bab054c4d9c2249048019e554
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09328110B2

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