Triethylamine → HCID 67519323, compound

HRID 1925460Notes

Reaction equation

HRID 1925460 reaction equation
Cl.Cl.[NH2:3][CH2:4][CH2:5][CH2:6][N:7]1[C:19]2[C:18]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[N:12]=[C:11]([NH2:20])[C:10]=2[N:9]=[C:8]1[CH2:21][CH2:22][O:23][CH3:24].C(N(CC)CC)C.[C:32](Cl)(=[O:36])[CH:33]([CH3:35])[CH3:34].C(=O)(O)[O-].[Na+]>N1C=CC=CC=1>[NH2:20][C:11]1[C:10]2[N:9]=[C:8]([CH2:21][CH2:22][O:23][CH3:24])[N:7]([CH2:6][CH2:5][CH2:4][NH:3][C:32](=[O:36])[CH:33]([CH3:35])[CH3:34])[C:19]=2[C:18]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[N:12]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 62325Isobutyryl chlorideHCID 516892Sodium BicarbonateHCID 675194151-(3-Aminopropyl)-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-4-amine dihydrochloride

Product 1

HCID 67519323HCID 67519323, compoundYield 104.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

1-(3-Aminopropyl)-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-4-amine dihydrochloride (6 g, 16 mmol) was combined with triethylamine (11.2 mL, 80 mmol) and pyridine (100 mL). Isobutyryl chloride (1.9 g, 18 mmol) was added dropwise and the reaction mixture was stirred at ambient temperature for 1 hour. The reaction mixture was combined with saturated aqueous sodium bicarbonate and extracted with dichloromethane (3×200 mL). The combined organics were dried over magnesium sulfate, filtered through a layer of CELITE filter aid, and then concentrated under reduced pressure to provide 6.2 g of crude N-{3-[4-amino-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl]propyl}-2-methylpropionamide as a brown solid.

Workup

  1. extractionextracted with dichloromethane (3×200 mL)
  2. dry with materialThe combined organics were dried over magnesium sulfate
  3. filtrationfiltered through a layer of CELITE
  4. filtrationfilter aid
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9e3f909b1902444b90ba304eaea3c35c
Source dataset
uspto-grants-2012_05
Patent number
US08178677B2

Reaction notes

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