3-Methoxypropylamine → 2-(5-(2-((3-Fluorophenyl)amino)-4-((3-methoxypropyl)amino)pyrimidin-5-yl)-4-pentyn-1-yl)isoindoline-1,3-dione

HRID 2284758ノート

反応式

HRID 2284758 の反応式
Cl[C:2]1[C:7]([C:8]#[C:9][CH2:10][CH2:11][CH2:12][N:13]2[C:21](=[O:22])[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14]2=[O:23])=[CH:6][N:5]=[C:4]([NH:24][C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([F:31])[CH:26]=2)[N:3]=1.C(N(CC)CC)C.[CH3:39][O:40][CH2:41][CH2:42][CH2:43][NH2:44].C(OCC)(=O)C>O1CCOCC1.O>[F:31][C:27]1[CH:26]=[C:25]([NH:24][C:4]2[N:3]=[C:2]([NH:44][CH2:43][CH2:42][CH2:41][O:40][CH3:39])[C:7]([C:8]#[C:9][CH2:10][CH2:11][CH2:12][N:13]3[C:21](=[O:22])[C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[C:14]3=[O:23])=[CH:6][N:5]=2)[CH:30]=[CH:29][CH:28]=1

参加物

7

反応物 4

HCID 16723-MethoxypropylamineHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 900523502-(5-(4-Chloro-2-((3-fluorophenyl)amino)pyrimidin-5-yl)-4-pentyn-1-yl)isoindoline-1,3-dione

生成物 1

HCID 900523172-(5-(2-((3-Fluorophenyl)amino)-4-((3-methoxypropyl)amino)pyrimidin-5-yl)-4-pentyn-1-yl)isoindoline-1,3-dione

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
50 °C

実験手順

To a solution of 2-(5-(4-chloro-2-((3-fluorophenyl)amino)pyrimidin-5-yl)-4-pentyn-1-yl)isoindoline-1,3-dione (J5, 124 mg) in 1,4-dioxane (2 mL), triethylamine (119 μL) and 3-methoxypropylamine (88 μL) were added at room temperature, and the mixture was stirred overnight at 50° C. in a sealed tube. The reaction mixture was cooled to room temperature, and then ethyl acetate and water were added to the reaction mixture. The organic layer was separated, washed successively with water and saturated aqueous sodium chloride, and then dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 2-(5-(2-((3-fluorophenyl)amino)-4-((3-methoxypropyl)amino)pyrimidin-5-yl)-4-pentyn-1-yl)isoindoline-1,3-dione (J6, 90 mg) as pale yellow solid.

後処理

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customThe organic layer was separated
  3. washwashed successively with water and saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-de2af69fc4804799b37d86c03dce2fd4
出典データセット
uspto-grants-2015_09
特許番号
US09145415B2

反応ノート

読み込み中…