7-benzyloxy-2-ethoxymethyl-N-isopropyl-1H-imidazo[4,5-c]quinoline-1,4-diamine → 4-amino-2-ethoxymethyl-1-isopropylamino-1H-imidazo[4,5-c]quinolin-7-ol

HRID 1373963Notes

Reaction equation

HRID 1373963 reaction equation
C([O:8][C:9]1[CH:10]=[CH:11][C:12]2[C:13]3[N:22]([NH:23][CH:24]([CH3:26])[CH3:25])[C:21]([CH2:27][O:28][CH2:29][CH3:30])=[N:20][C:14]=3[C:15]([NH2:19])=[N:16][C:17]=2[CH:18]=1)C1C=CC=CC=1>C1(C)C=CC=CC=1.CO.[Pd]>[NH2:19][C:15]1[C:14]2[N:20]=[C:21]([CH2:27][O:28][CH2:29][CH3:30])[N:22]([NH:23][CH:24]([CH3:26])[CH3:25])[C:13]=2[C:12]2[CH:11]=[CH:10][C:9]([OH:8])=[CH:18][C:17]=2[N:16]=1

Participants

5

Reactant 1

HCID 100926957-benzyloxy-2-ethoxymethyl-N-isopropyl-1H-imidazo[4,5-c]quinoline-1,4-diamine

Product 1

HCID 1354103774-amino-2-ethoxymethyl-1-isopropylamino-1H-imidazo[4,5-c]quinolin-7-olYield 38.5%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 1140TolueneSolvent

Procedure

A solution of 7-benzyloxy-2-ethoxymethyl-N1-isopropyl-1H-imidazo[4,5-c]quinoline-1,4-diamine (1.67 g, 4.12 mmol) in 25 mL of toluene and 25 mL of methanol was treated with palladium on carbon (0.44 g, 0.42 mmol, 10% w/w). The mixture was shaken under an atmosphere of hydrogen (3.8×105 Pa). After 16 h, the reaction was filtered through a pad of CELITE filter agent and rinsed with solvent until the filtrate ran clear. The filtrate was concentrated under reduced pressure to provide a white solid. Purification by chromatography (SiO2, 3:1 CHCl3:(80:18:2 CHCl3:MeOH:NH4OH) gradient to 1:1) gave 0.50 g of 4-amino-2-ethoxymethyl-1-isopropylamino-1H-imidazo[4,5-c]quinolin-7-ol as a white solid. MS (APCI) m/z 316 (M+H)+.

Workup

  1. filtrationthe reaction was filtered through a pad of CELITE
  2. filtrationfilter agent
  3. washrinsed with solvent until the filtrate
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customto provide a white solid
  6. customPurification by chromatography (SiO2, 3:1 CHCl3:(80:18:2 CHCl3:MeOH:NH4OH) gradient to 1:1)

Sources & evidence

ORD record
ord-5d33fba37a764203ab78e0391bb5b7e3
Source dataset
uspto-grants-2007_01
Patent number
US07163947B2

Reaction notes

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