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

HRID 2362572Notes

Reaction equation

HRID 2362572 reaction equation
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]

Participants

6

Reactant 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

Product 1

HCID 86611639N-methoxy-N-methyl-5-(2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)pentanamideYield 92.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-5820da058fae4a1bb57902b8b611f18e
Source dataset
uspto-grants-2014_04
Patent number
US08691837B2

Reaction notes

Loading…