Ethanol → 3-[4-amino-2-ethyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-imidazo[4,5-c]quinolin-7-yl]-N,N-dimethylpropanamide

HRID 244882Notes

Reaction equation

HRID 244882 reaction equation
C(O)C.[NH2:4][C:5]1[C:14]2[N:15]=[C:16]([CH2:25][CH3:26])[N:17]([CH2:18][CH:19]3[CH2:24][CH2:23][O:22][CH2:21][CH2:20]3)[C:13]=2[C:12]2[CH:11]=[CH:10][C:9](/[CH:27]=[CH:28]/[C:29]([N:31]([CH3:33])[CH3:32])=[O:30])=[CH:8][C:7]=2[N:6]=1>[Pd].CO>[NH2:4][C:5]1[C:14]2[N:15]=[C:16]([CH2:25][CH3:26])[N:17]([CH2:18][CH:19]3[CH2:20][CH2:21][O:22][CH2:23][CH2:24]3)[C:13]=2[C:12]2[CH:11]=[CH:10][C:9]([CH2:27][CH2:28][C:29]([N:31]([CH3:32])[CH3:33])=[O:30])=[CH:8][C:7]=2[N:6]=1

Participants

5

Reactant 2

HCID 702EthanolHCID 57657266(2E)-3-[4-amino-2-ethyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-imidazo[4,5-c]quinolin-7-yl]-N,N-dimethylprop-2-enamide

Product 1

HCID 576572373-[4-amino-2-ethyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-imidazo[4,5-c]quinolin-7-yl]-N,N-dimethylpropanamideYield 68.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A glass Parr bottle was charged with 10% palladium on carbon (0.1 g) wetted with ethanol (10 mL) and a slurry of (2E)-3-[4-amino-2-ethyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-imidazo[4,5-c]quinolin-7-yl]-N,N-dimethylprop-2-enamide (0.32 g, 0.78 mmol) in methanol (200 mL). The vessel was placed on Parr apparatus, evacuated and charged with hydrogen (55 psi). The mixture was shaken at ambient temperature for 48 hours. The reaction mixture was filtered through a 0.2 micron PTFE membrane filter and the filter was rinsed with methanol (100 mL). The filtrate was concentrated to dryness under reduced pressure. The resulting solid was recrystallized from acetonitrile to provide 220 mg of 3-[4-amino-2-ethyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-imidazo[4,5-c]quinolin-7-yl]-N,N-dimethylpropanamide as a white crystalline solid, mp 219-220° C.

Workup

  1. customevacuated
  2. additioncharged with hydrogen (55 psi)
  3. filtrationThe reaction mixture was filtered through a 0.2 micron PTFE membrane
  4. filtrationfilter
  5. washthe filter was rinsed with methanol (100 mL)
  6. concentrationThe filtrate was concentrated to dryness under reduced pressure
  7. customThe resulting solid was recrystallized from acetonitrile

Sources & evidence

ORD record
ord-874d664fc3bd4326885c37e24acb3d53
Source dataset
uspto-grants-2014_02
Patent number
US08658666B2

Reaction notes

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