Triethylamine → HCID 67519323, compound

HRID 81885Notes

Reaction equation

HRID 81885 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-b64d6318beb54550bb802c47afaf28f0
Source dataset
uspto-grants-2014_09
Patent number
US08846710B2

Reaction notes

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