Triethylamine → 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

HRID 244868ノート

反応式

HRID 244868 の反応式
[CH:1]([N:3]1[C:7](=[O:8])[C:6]2=[CH:9][CH:10]=[CH:11][CH:12]=[C:5]2[C:4]1=[O:13])=[CH2:2].C(N(CC)CC)C.Br[C:22]1[CH:31]=[CH:30][C:29]2[N:28]=[CH:27][C:26]3[N:32]=[C:33]([CH2:44][CH2:45][O:46][CH3:47])[N:34]([CH2:35][CH2:36][CH2:37][N:38]4[CH2:42][CH2:41][CH2:40][C:39]4=[O:43])[C:25]=3[C:24]=2[CH:23]=1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(#N)C>[CH3:47][O:46][CH2:45][CH2:44][C:33]1[N:34]([CH2:35][CH2:36][CH2:37][N:38]2[CH2:42][CH2:41][CH2:40][C:39]2=[O:43])[C:25]2[C:24]3[CH:23]=[C:22]([CH:2]=[CH:1][N:3]4[C:7](=[O:8])[C:6]5[C:5](=[CH:12][CH:11]=[CH:10][CH:9]=5)[C:4]4=[O:13])[CH:31]=[CH:30][C:29]=3[N:28]=[CH:27][C:26]=2[N:32]=1

参加物

7

反応物 3

HCID 8471TriethylamineHCID 770351H-Isoindole-1,3(2H)-dione, 2-ethenyl-HCID 219843071-{3-[8-bromo-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl]propyl}pyrrolidin-2-one

生成物 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収率 101.6%

試薬・触媒・溶媒 3

HCID 80271Tri-o-tolylphosphine触媒HCID 167845palladium(II) acetate触媒HCID 6342Acetonitrile溶媒

反応条件

温度
120 °C

実験手順

A thick walled glass tube, equipped with a stir bar, was charged with palladium (II) acetate (17 mg, 0.08 mmol), acetonitrile (50 mL), N-vinylphthalimide (716 mg, 4.13 mmol), triethylamine (1.6 mL, 11 mmol), tri-o-tolylphosphine (69 mg, 0.22 mmol) and 1-{3-[8-bromo-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl]propyl}pyrrolidin-2-one (1.62 g, 3.76 mmol). The reaction mixture was purged with nitrogen and the tube was sealed and heated at 120° C. in an oil bath for 15 hours. The reaction was cooled to ambient temperature and methanol (50 mL) and chloroform (50 ml) were added. After filtering through a 0.2 micron PTFE membrane, the solution was concentrated under reduced pressure and then purified by chromatography using a HORIZON HPFC system (silica cartridge, eluting with a 0-8% gradient of methanol in dichloromethane) to provide 2.0 g of 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 as a bright yellow solid.

後処理

  1. customA thick walled glass tube, equipped with a stir bar
  2. customThe reaction mixture was purged with nitrogen
  3. customthe tube was sealed
  4. temperatureThe reaction was cooled to ambient temperature
  5. additionmethanol (50 mL) and chloroform (50 ml) were added
  6. filtrationAfter filtering through a 0.2 micron PTFE membrane
  7. concentrationthe solution was concentrated under reduced pressure
  8. custompurified by chromatography
  9. washeluting with a 0-8% gradient of methanol in dichloromethane)

出典と根拠

ORDレコード
ord-14ff085203a346ac8f5fbe8d490f62ad
出典データセット
uspto-grants-2014_02
特許番号
US08658666B2

反応ノート

読み込み中…