4-Morpholinecarbonyl chloride → HCID 58833636, compound

HRID 540831Notes

Reaction equation

HRID 540831 reaction equation
[NH2:1][CH2:2][CH2:3][O:4][C:5]1[CH:6]=[CH:7][C:8]2[C:9]3[N:18]([CH2:19][CH:20]([CH3:22])[CH3:21])[C:17]([CH3:23])=[N:16][C:10]=3[C:11]([NH2:15])=[N:12][C:13]=2[CH:14]=1.[N:24]1([C:30](Cl)=[O:31])[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1>C(Cl)(Cl)Cl>[NH2:15][C:11]1[C:10]2[N:16]=[C:17]([CH3:23])[N:18]([CH2:19][CH:20]([CH3:21])[CH3:22])[C:9]=2[C:8]2[CH:7]=[CH:6][C:5]([O:4][CH2:3][CH2:2][NH:1][C:30]([N:24]3[CH2:29][CH2:28][O:27][CH2:26][CH2:25]3)=[O:31])=[CH:14][C:13]=2[N:12]=1

Participants

4

Reactant 2

HCID 848104-Morpholinecarbonyl chlorideHCID 58833728HCID 58833728, compound

Product 1

HCID 58833636HCID 58833636, compoundYield 37.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

A suspension of 7-(2-aminoethoxy)-2-methyl-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-4-amine (0.300 g, 0.958 mmol) in chloroform (10 mL) was cooled to 0° C. 4-Morpholinecarbonyl chloride (0.110 mL, 0.942 mmol) was added dropwise, and the reaction was stirred for five minutes at 0° C. The reaction was then allowed to warm to ambient temperature over a period of 15 minutes, and the solvent was removed under reduced pressure. The resulting off-white solid was dissolved in dichloromethane. The solution was washed sequentially with 10% aqueous sodium hydroxide, water, and brine; dried over magnesium sulfate; filtered; and concentrated under reduced pressure. The residue was recrystallized from acetonitrile to provide 0.150 g of N-(2-{[4-amino-2-methyl-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-7-yl]oxy}ethyl)morpholine-4-carboxamide as a white powder, mp 215-219° C. (decomposition).

Workup

  1. temperatureto warm to ambient temperature over a period of 15 minutes
  2. customthe solvent was removed under reduced pressure
  3. dissolutionThe resulting off-white solid was dissolved in dichloromethane
  4. washThe solution was washed sequentially with 10% aqueous sodium hydroxide, water, and brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationand concentrated under reduced pressure
  8. customThe residue was recrystallized from acetonitrile

Sources & evidence

ORD record
ord-045bd52bbca840dca50c4de67ae5e843
Source dataset
uspto-grants-2014_10
Patent number
US08871782B2

Reaction notes

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