Sodium Carbonate → HCID 68971706, compound

HRID 540898Notes

Reaction equation

HRID 540898 reaction equation
[C:1](Cl)(=[O:5])[CH:2]([CH3:4])[CH3:3].[NH2:7][CH2:8][CH2:9][CH2:10][O:11][C:12]1[CH:13]=[CH:14][C:15]2[C:16]3[N:25]([CH2:26][CH2:27][CH3:28])[C:24]([CH2:29][CH2:30][O:31][CH3:32])=[N:23][C:17]=3[C:18]([NH2:22])=[N:19][C:20]=2[CH:21]=1.C(=O)([O-])[O-].[Na+].[Na+]>ClCCl>[NH2:22][C:18]1[C:17]2[N:23]=[C:24]([CH2:29][CH2:30][O:31][CH3:32])[N:25]([CH2:26][CH2:27][CH3:28])[C:16]=2[C:15]2[CH:14]=[CH:13][C:12]([O:11][CH2:10][CH2:9][CH2:8][NH:7][C:1](=[O:5])[CH:2]([CH3:4])[CH3:3])=[CH:21][C:20]=2[N:19]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 62325Isobutyryl chlorideHCID 58833621HCID 58833621, compound

Product 1

HCID 68971706HCID 68971706, compoundYield 74.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

Isobutyryl chloride (0.375 nL, 3.58 mmol) was added dropwise to a slurry of 7-(3-aminopropoxy)-2-(2-methoxyethyl)-1-propyl-1H-imidazo[4,5-c]quinolin-4-amine (prepared as described in Example 394, 1.28 g, 3.58 mmol) in dichloromethane (22 mL) at 0° C. The reaction mixture was allowed to stir for 30 minutes at 0° C., then the reaction mixture was allowed to stir for 16 hours at ambient temperature. Saturated aqueous sodium carbonate was added and the reaction mixture was stirred for 1 hour, resulting in the formation of a flocculent solid. The solid was isolated by filtration and dissolved in dichloromethane. The dichloromethane was washed with water and saturated aqueous sodium chloride, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The resulting white solid was recrystallized from acetonitrile to afford 1.14 g of N-(3-{[4-amino-2-(2-methoxyethyl)-1-propyl-1H-imidazo[4,5-c]quinolin-7-yl]oxy}propyl)-2-methylpropanamide as an off-white solid.

Workup

  1. stirringto stir for 16 hours at ambient temperature
  2. stirringthe reaction mixture was stirred for 1 hour
  3. customresulting in the formation of a flocculent solid
  4. customThe solid was isolated by filtration
  5. washThe dichloromethane was washed with water and saturated aqueous sodium chloride
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe resulting white solid was recrystallized from acetonitrile

Sources & evidence

ORD record
ord-9540dd94498642e5bedd5b3724a5c2ee
Source dataset
uspto-grants-2014_10
Patent number
US08871782B2

Reaction notes

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