Sodium Bicarbonate → 1-ethyl-3-[1-(1-methyl-1H-benzimidazol-2-yl)-2,3-dihydro-1H-indol-5-yl]-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one

HRID 587468

反応式

HRID 587468 の反応式
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([N:10]3[C:14]4=[N:15][CH:16]=[CH:17][CH:18]=[C:13]4[N:12]([CH2:19][CH3:20])[C:11]3=[O:21])=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.Cl[C:23]1[N:27]([CH2:28]OCC[Si](C)(C)C)[C:26]2[CH:36]=[CH:37][CH:38]=[CH:39][C:25]=2[N:24]=1.C([O-])(O)=O.[Na+]>CN1C(=O)CCC1>[CH2:19]([N:12]1[C:13]2[C:14](=[N:15][CH:16]=[CH:17][CH:18]=2)[N:10]([C:6]2[CH:5]=[C:4]3[C:9](=[CH:8][CH:7]=2)[N:1]([C:23]2[N:27]([CH3:28])[C:26]4[CH:36]=[CH:37][CH:38]=[CH:39][C:25]=4[N:24]=2)[CH2:2][CH2:3]3)[C:11]1=[O:21])[CH3:20]

参加物

5

反応物 3

HCID 516892Sodium BicarbonateHCID 585772823-(2,3-dihydro-1H-indol-5-yl)-1-ethyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-oneHCID 597528982-Chloro-1-[[2-(trimethylsilanyl)ethoxy]methyl]-benzimidazole

生成物 1

HCID 585776601-ethyl-3-[1-(1-methyl-1H-benzimidazol-2-yl)-2,3-dihydro-1H-indol-5-yl]-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one収率 8.2%

試薬・触媒・溶媒 1

HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
120 °C

実験手順

A mixture of 3-(2,3-dihydro-1H-indol-5-yl)-1-ethyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (100 mg) and 2-chloro-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-benzimidazole (101 mg) in NMP (2 mL) was stirred at 120° C. for 10 h, treated with saturated NaHCO3 solution and extracted with AcOEt. The organic layer was dried over MgSO4 and concentrated in vacuo. The residue was dissolved in DMF (2 mL), and then iodomethane (0.022 mL) and Cs2CO3 (0.176 g) were added. The mixture was stirred at room temperature for 3 h, treated with water and extracted with AcOEt. The organic layer was dried over MgSO4 and concentrated in vacuo. The residue was suspended in CH3CN and the precipitate was filtered off. The residue was purified by prep. HPLC, and then chromatographed on silica gel eluting with AcOEt/Hexane. Crystallization from AcOEt/Hexane gave the title compound (12 mg).

後処理

  1. extractionextracted with AcOEt
  2. dry with materialThe organic layer was dried over MgSO4
  3. concentrationconcentrated in vacuo
  4. dissolutionThe residue was dissolved in DMF (2 mL)
  5. additioniodomethane (0.022 mL) and Cs2CO3 (0.176 g) were added
  6. stirringThe mixture was stirred at room temperature for 3 h
  7. additiontreated with water
  8. extractionextracted with AcOEt
  9. dry with materialThe organic layer was dried over MgSO4
  10. concentrationconcentrated in vacuo
  11. filtrationthe precipitate was filtered off
  12. customThe residue was purified by prep
  13. customHPLC, and then chromatographed on silica gel eluting with AcOEt/Hexane
  14. customCrystallization from AcOEt/Hexane

出典と根拠

ORDレコード
ord-205d0c7c30cb4a0cbff2f21be5dfcb98
出典データセット
uspto-grants-2016_01
特許番号
US09226921B2

関連ノート

読み込み中…