2-(2-{2-(2-methoxyethyl)-1-[3-(2-oxopyrrolidin-1-yl)propyl]-1H-imidazo[4,5-c]quinolin-8-yl}ethenyl)-1H-isoindole-1,3(2H)-dione → 2-(2-{2-(2-methoxyethyl)-1-[3-(2-oxo-pyrrolidin-1-yl)propyl]-1H-imidazo[4,5-c]quinolin-8-yl}ethyl)-1H-isoindole-1,3(2H)-dione

HRID 244869Notes

Reaction equation

HRID 244869 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][C:5]1[N:6]([CH2:31][CH2:32][CH2:33][N:34]2[CH2:38][CH2:37][CH2:36][C:35]2=[O:39])[C:7]2[C:16]3[CH:15]=[C:14]([CH:17]=[CH:18][N:19]4[C:27](=[O:28])[C:26]5[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=5)[C:20]4=[O:29])[CH:13]=[CH:12][C:11]=3[N:10]=[CH:9][C:8]=2[N:30]=1>[Pd].CO>[CH3:1][O:2][CH2:3][CH2:4][C:5]1[N:6]([CH2:31][CH2:32][CH2:33][N:34]2[CH2:38][CH2:37][CH2:36][C:35]2=[O:39])[C:7]2[C:16]3[CH:15]=[C:14]([CH2:17][CH2:18][N:19]4[C:20](=[O:29])[C:21]5[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=5)[C:27]4=[O:28])[CH:13]=[CH:12][C:11]=3[N:10]=[CH:9][C:8]=2[N:30]=1

Participants

4

Reactant 1

HCID 690814342-(2-{2-(2-methoxyethyl)-1-[3-(2-oxopyrrolidin-1-yl)propyl]-1H-imidazo[4,5-c]quinolin-8-yl}ethenyl)-1H-isoindole-1,3(2H)-dione

Product 1

HCID 690772482-(2-{2-(2-methoxyethyl)-1-[3-(2-oxo-pyrrolidin-1-yl)propyl]-1H-imidazo[4,5-c]quinolin-8-yl}ethyl)-1H-isoindole-1,3(2H)-dioneYield 105.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

A glass Parr vessel was charged with 10% palladium on carbon (0.2 g), methanol (75 mL) and 2-(2-{2-(2-methoxyethyl)-1-[3-(2-oxopyrrolidin-1-yl)propyl]-1H-imidazo[4,5-c]quinolin-8-yl}ethenyl)-1H-isoindole-1,3(2H)-dione (2.0 g, 3.8 mmol). The vessel was evacuated and charged with hydrogen gas (40 psi, 2.8×105 Pa). The reaction was shaken at 50° C. for approximately 18 hours. After cooling to ambient temperature, the reaction mixture was filtered followed by concentration under reduced pressure to provide 2.1 g of 2-(2-{2-(2-methoxyethyl)-1-[3-(2-oxo-pyrrolidin-1-yl)propyl]-1H-imidazo[4,5-c]quinolin-8-yl}ethyl)-1H-isoindole-1,3(2H)-dione as a pale yellow solid. MS (ESI) m/z 526 (M+H)+.

Workup

  1. customThe vessel was evacuated
  2. additioncharged with hydrogen gas (40 psi, 2.8×105 Pa)
  3. temperatureAfter cooling to ambient temperature
  4. filtrationthe reaction mixture was filtered
  5. concentrationfollowed by concentration under reduced pressure

Sources & evidence

ORD record
ord-8a07544081e24b5db41a43918738a51a
Source dataset
uspto-grants-2014_02
Patent number
US08658666B2

Reaction notes

Loading…