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Acetic Acid → 4-[5-(4-fluorophenyl)-1-methyl-3-oxido-2-phenyl-1H-imidazol-4-yl]pyridin-2(1H)-one

HRID 23525
ノート
印刷プレビュー

反応式

HRID 23525 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[C:9]([C:12]2[CH:17]=[CH:16][N:15]=C(F)C=2)=[N:10][OH:11])=[CH:4][CH:3]=1.[CH:20](=O)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[CH3:28][NH2:29].[C:30]([OH:33])(=O)[CH3:31]>C(Cl)Cl.CO>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:29]([CH3:28])[C:20]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[N+:10]([O-:11])[C:9]=2[C:12]2[CH:17]=[CH:16][NH:15][C:30](=[O:33])[CH:31]=2)=[CH:6][CH:7]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 176Acetic AcidHCID 240BenzaldehydeHCID 6329MethylamineHCID 1363357801-(2-Fluoropyridin-4-yl)-2-(4-fluorophenyl)ethane-1,2-dione-1-oxime

生成物 1

HCID 695576504-[5-(4-fluorophenyl)-1-methyl-3-oxido-2-phenyl-1H-imidazol-4-yl]pyridin-2(1H)-one

試薬・触媒・溶媒 1

HCID 21226129
Dichloromethane methanol
溶媒

反応条件

温度
100 °C

実験手順

To a suspension of 1-(4-fluorophenyl)-2-(2-fluoropyridin-4-yl)ethane-1,2-dione 2-oxime (Example 1, Step B) (400 mg, 1.52 mmol) in acetic acid (7.6 mL) was added benzaldehyde (170 μL, 1.68 mmol) followed by methylamine (144 μL, 40 wt. % in H2O, 1.68 mmol), and the mixture was heated for 41 hours at 100° C. It was cooled and acetic acid was removed in vacuo. The residue was taken up in H2O and was concentrated in vacuo two times. This was repeated with toluene to obtain crude residue. The crude residue was dissolved in a mixture of CH2Cl2/MeOH, filtered off solid (unreacted, hydrolyzed imidazole), and the solvent was removed in vacuo. The crude product was pre-absorbed on silica gel and purified by flash chromatography eluting with 5% MeOH/CH2Cl2 followed by 10% 2M NH3 in MeOH/CH2Cl2 to obtain 270 mg of the title compound.

後処理

  1. temperatureIt was cooled
  2. customacetic acid was removed in vacuo
  3. concentrationwas concentrated in vacuo two times
  4. customto obtain crude residue
  5. filtrationfiltered off solid (unreacted, hydrolyzed imidazole)
  6. customthe solvent was removed in vacuo
  7. customThe crude product was pre-absorbed on silica gel
  8. custompurified by flash chromatography
  9. washeluting with 5% MeOH/CH2Cl2

出典と根拠

ORDレコード
ord-1e70f435aee645cbb542fdc2092f5543
出典データセット
uspto-grants-2005_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06852727B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート