2-{(3E)-4-[2-ethoxymethyl-1-(3-isopropoxypropyl)-1H-imidazo[4,5-c]quinolin-7-yl]but-3-enyl}-1H-isoindole-1,3(2H)-dione → 2-{4-[2-ethoxymethyl-1-(3-isopropoxypropyl)-1H-imidazo[4,5-c]quinolin-7-yl]butyl}-1H-isoindole-1,3(2H)-dione

HRID 244816

Reaction equation

HRID 244816 reaction equation
[CH2:1]([O:3][CH2:4][C:5]1[N:6]([CH2:33][CH2:34][CH2:35][O:36][CH:37]([CH3:39])[CH3:38])[C:7]2[C:16]3[CH:15]=[CH:14][C:13](/[CH:17]=[CH:18]/[CH2:19][CH2:20][N:21]4[C:29](=[O:30])[C:28]5[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=5)[C:22]4=[O:31])=[CH:12][C:11]=3[N:10]=[CH:9][C:8]=2[N:32]=1)[CH3:2]>C(O)C.[Pd]>[CH2:1]([O:3][CH2:4][C:5]1[N:6]([CH2:33][CH2:34][CH2:35][O:36][CH:37]([CH3:38])[CH3:39])[C:7]2[C:16]3[CH:15]=[CH:14][C:13]([CH2:17][CH2:18][CH2:19][CH2:20][N:21]4[C:22](=[O:31])[C:23]5[C:28](=[CH:27][CH:26]=[CH:25][CH:24]=5)[C:29]4=[O:30])=[CH:12][C:11]=3[N:10]=[CH:9][C:8]=2[N:32]=1)[CH3:2]

Participants

4

Reactant 1

HCID 690842002-{(3E)-4-[2-ethoxymethyl-1-(3-isopropoxypropyl)-1H-imidazo[4,5-c]quinolin-7-yl]but-3-enyl}-1H-isoindole-1,3(2H)-dione

Product 1

HCID 690814062-{4-[2-ethoxymethyl-1-(3-isopropoxypropyl)-1H-imidazo[4,5-c]quinolin-7-yl]butyl}-1H-isoindole-1,3(2H)-dioneYield 99.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Procedure

2-{(3E)-4-[2-ethoxymethyl-1-(3-isopropoxypropyl)-1H-imidazo[4,5-c]quinolin-7-yl]but-3-enyl}-1H-isoindole-1,3(2H)-dione (1.9 g, 3.6 mmol) was dissolved in ethanol (50 mL) and added to a Parr flask containing 10% palladium on carbon (0.3 g) wetted with ethanol. The flask was degassed three times, charged with hydrogen (50 psi) and shaken for 16 hours. The catalyst was removed by filtration through CELITE filter agent. Concentration of the filtrate under reduced pressure provided 1.9 g of 2-{4-[2-ethoxymethyl-1-(3-isopropoxypropyl)-1H-imidazo[4,5-c]quinolin-7-yl]butyl}-1H-isoindole-1,3(2H)-dione as a pale yellow oil.

Workup

  1. additionadded to a Parr flask
  2. customThe flask was degassed three times
  3. additioncharged with hydrogen (50 psi)
  4. customThe catalyst was removed by filtration through CELITE
  5. filtrationfilter agent

Sources & evidence

ORD record
ord-205a6d5e0f914bb3a296fb93a357eac6
Source dataset
uspto-grants-2014_02
Patent number
US08658666B2

Linked notes

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