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

HRID 540932Notes

Reaction equation

HRID 540932 reaction equation
C([O:8][C:9]1[CH:10]=[CH:11][C:12]2[C:13]3[N:22]([CH2:23][CH:24]4[CH2:29][CH2:28][O:27][CH2:26][CH2:25]4)[C:21]([CH2:30][CH3:31])=[N:20][C:14]=3[C:15]([NH2:19])=[N:16][C:17]=2[CH:18]=1)C1C=CC=CC=1.C(O)C.CO>[Pd].ClCCl>[NH2:19][C:15]1[C:14]2[N:20]=[C:21]([CH2:30][CH3:31])[N:22]([CH2:23][CH:24]3[CH2:29][CH2:28][O:27][CH2:26][CH2:25]3)[C:13]=2[C:12]2[CH:11]=[CH:10][C:9]([OH:8])=[CH:18][C:17]=2[N:16]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 887MethanolHCID 689736207-benzyloxy-2-ethyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-imidazo[4,5-c]quinolin-4-amine

Product 1

HCID 1363478564-amino-2-ethyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-imidazo[4,5-c]quinolin-7-olYield 71%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 7-benzyloxy-2-ethyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-imidazo[4,5-c]quinolin-4-amine (1.76 g, 4.23 mmol), palladium on carbon (1 g), and ethanol (50 mL) was shaken under hydrogen pressure (50 psi, 3.4×105 Pa) on a Parr apparatus overnight. The reaction mixture was diluted with dichloromethane (75 mL) and then filtered through a layer of CELITE filter agent. The filter cake was rinsed with 25% methanol in chloroform (400 mL). The combined filtrates were concentrated under reduced pressure to provide a white solid. This material was slurried with methanol, isolated by filtration, and dried under vacuum to provide 0.98 g of 4-amino-2-ethyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-imidazo[4,5-c]quinolin-7-ol.

Workup

  1. filtrationfiltered through a layer of CELITE filter agent
  2. washThe filter cake was rinsed with 25% methanol in chloroform (400 mL)
  3. concentrationThe combined filtrates were concentrated under reduced pressure
  4. customto provide a white solid
  5. customisolated by filtration
  6. customdried under vacuum

Sources & evidence

ORD record
ord-c56408929e284627ae32187aee0dbada
Source dataset
uspto-grants-2014_10
Patent number
US08871782B2

Reaction notes

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