Dipropylamine → 2-(4-Fluorophenyl)-N,N-dipropyl-3H-imidazo[4,5-b]pyridine-3-acetamide

HRID 1709595ノート

反応式

HRID 1709595 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:16]([CH2:17][C:18]([OH:20])=O)[C:11]3=[N:12][CH:13]=[CH:14][CH:15]=[C:10]3[N:9]=2)=[CH:4][CH:3]=1.[CH2:21]([NH:24][CH2:25][CH2:26][CH3:27])[CH2:22][CH3:23]>O1CCCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:16]([CH2:17][C:18]([N:24]([CH2:25][CH2:26][CH3:27])[CH2:21][CH2:22][CH3:23])=[O:20])[C:11]3=[N:12][CH:13]=[CH:14][CH:15]=[C:10]3[N:9]=2)=[CH:6][CH:7]=1

参加物

4

反応物 2

HCID 8902DipropylamineHCID 156171894-fluorophenyl-3H-imidazo[4,5-b]pyridine-3-acetic acid

生成物 1

HCID 143903992-(4-Fluorophenyl)-N,N-dipropyl-3H-imidazo[4,5-b]pyridine-3-acetamide収率 34%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A mixture of 2-(4-fluorophenyl)-3H-imidazo[4,5-b]pyridine-3-acetic acid (5.0 g, 0.01845 mole) and 1,1'-carbonyldiimiazole (2.99 g, 0.01845 mole) was stirred at room temperature in dry tetrahydrofuran (100 ml) for three hours with a stream of nitrogen bubbling through it. A solution of dipropylamine (5.6 g, 0.0554 mole) in tetrahydrofuran (7 ml) was added and the reaction mixture was refluxed overnight under nitrogen. The solvents were removed under reduced pressure and the residue was triturated in 100 ml of water, the solid was collected by filtration, rinsed twice with water, twice with a 5% potassium hydroxide solution and twice again with water. The solid was dissolved in hot isopropyl alcohol, filtered hot, cooled to room temperature, and water was added to the cloud point. The resulting solid was collected by filtration, rinsed with water, and dried under high vacuum at 42° C. overnight to give 2.22 g (34%) of title compound, mp. 135°-136° C.

後処理

  1. temperaturethe reaction mixture was refluxed overnight under nitrogen
  2. customThe solvents were removed under reduced pressure
  3. customthe residue was triturated in 100 ml of water
  4. filtrationthe solid was collected by filtration
  5. washrinsed twice with water, twice with a 5% potassium hydroxide solution and twice again with water
  6. dissolutionThe solid was dissolved in hot isopropyl alcohol
  7. filtrationfiltered hot
  8. additionwater was added to the cloud point
  9. filtrationThe resulting solid was collected by filtration
  10. washrinsed with water
  11. customdried under high vacuum at 42° C. overnight

出典と根拠

ORDレコード
ord-0c14c21240e44e53bc215436ec22a59d
出典データセット
uspto-grants-1990_08
特許番号
US04948800

反応ノート

読み込み中…