Ammonia → 1-(2-Cyclopropyl-1-methyl-1H-benzimidazol-6-yl)-4-(phenylmethoxy)-2(1H)-pyridinone

HRID 2202847ノート

反応式

HRID 2202847 の反応式
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][NH:12][C:11](=[O:15])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[C:17]1[CH:18]=[CH:19][C:20]2[N:24]=[C:23]([CH:25]3[CH2:27][CH2:26]3)[N:22]([CH3:28])[C:21]=2[CH:29]=1.C(=O)([O-])[O-].[K+].[K+].CNCCNC.N>[Cu](I)I.CS(C)=O>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]([C:17]2[CH:18]=[CH:19][C:20]3[N:24]=[C:23]([CH:25]4[CH2:26][CH2:27]4)[N:22]([CH3:28])[C:21]=3[CH:29]=2)[C:11](=[O:15])[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

8

反応物 5

HCID 222AmmoniaHCID 8070N,N'-DimethylethylenediamineHCID 11430Potassium CarbonateHCID 36077244-Benzyloxy-2(1H)-pyridoneHCID 838254226-Bromo-2-cyclopropyl-1-methyl-1H-benzoimidazole

生成物 1

HCID 896910321-(2-Cyclopropyl-1-methyl-1H-benzimidazol-6-yl)-4-(phenylmethoxy)-2(1H)-pyridinone収率 54.2%

試薬・触媒・溶媒 2

HCID 83717Copper iodide触媒HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
150 °C

実験手順

A mixture of 4-(benzyloxy)pyridin-2(1H)-one (1.60 g), 6-bromo-2-cyclopropyl-1-methyl-1H-benzimidazole (2 g), potassium carbonate (3.30 g), N,N′-dimethylethylenediamine (0.855 ml), copper iodide (1.52 g) and DMSO (40 ml) was stirred at 150° C. under Ar atmosphere for 1 h. The mixture was poured into 28% NH3 solution. The precipitate was collected by filtration and washed with water and EtOAc. The solid was dissolved in THF, put on through silica gel pad and concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/MeOH). The resulting solid was dissolved in MeOH, and stirred with activated charcoal at room temperature for 10 min. The insoluble material was removed by filtration, and the filtrate was concentrated in vacuo to give the title compound (1.60 g) as an off-white solid.

後処理

  1. filtrationThe precipitate was collected by filtration
  2. washwashed with water and EtOAc
  3. dissolutionThe solid was dissolved in THF
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica gel column chromatography (EtOAc/MeOH)
  6. dissolutionThe resulting solid was dissolved in MeOH
  7. stirringstirred with activated charcoal at room temperature for 10 min
  8. customThe insoluble material was removed by filtration
  9. concentrationthe filtrate was concentrated in vacuo

出典と根拠

ORDレコード
ord-f671287c57ed4c5cab1748e60f8df828
出典データセット
uspto-grants-2016_06
特許番号
US09365540B2

反応ノート

読み込み中…