Water → 4-((5-(5-(1,3-Dioxoisoindolin-2-yl)-1-pentyn-1-yl)-4-((4-fluorophenyl)amino)pyrimidin-2-yl)amino)benzonitrile

HRID 2284766노트

반응식

HRID 2284766 반응식
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:32]=[CH:31][C:28]([C:29]#[N:30])=[CH:27][CH:26]=2)[N:3]=1.C(OCC)(=O)C.O.[F:40][C:41]1[CH:47]=[CH:46][C:44]([NH2:45])=[CH:43][CH:42]=1>O1CCOCC1.C(N(CC)CC)C>[O:23]=[C:14]1[C:15]2[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:21](=[O:22])[N:13]1[CH2:12][CH2:11][CH2:10][C:9]#[C:8][C:7]1[C:2]([NH:45][C:44]2[CH:46]=[CH:47][C:41]([F:40])=[CH:42][CH:43]=2)=[N:3][C:4]([NH:24][C:25]2[CH:32]=[CH:31][C:28]([C:29]#[N:30])=[CH:27][CH:26]=2)=[N:5][CH:6]=1

참가 물질

7

반응물 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 97314-FluoroanilineHCID 900521494-((4-Chloro-5-(5-(1,3-dioxoisoindolin-2-yl)-1-pentyn-1-yl)pyrimidin-2-yl)amino)benzonitrile

생성물 1

HCID 900523024-((5-(5-(1,3-Dioxoisoindolin-2-yl)-1-pentyn-1-yl)-4-((4-fluorophenyl)amino)pyrimidin-2-yl)amino)benzonitrile

시약·촉매·용매 2

HCID 8471Triethylamine용매HCID 312751,4-Dioxane용매

반응 조건

온도
95 °C

실험 절차

To a solution of 4-((4-chloro-5-(5-(1,3-dioxoisoindolin-2-yl)-1-pentyn-1-yl)pyrimidin-2-yl)amino)benzonitrile (J13, 41 mg) in 1,4-dioxane (1.5 mL), 4-fluoroaniline (79 μL) and triethylamine (115 μL) were added at room temperature, and the mixture was stirred at 95° C. for 2 hours 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 1.0 mol/L aqueous hydrochloric acid, saturated aqueous sodium hydrogencarbonate and saturated aqueous sodium chloride, and then dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained solid matter was washed with a mixed solvent of chloroform and methanol, and then dried under reduced pressure to obtain 4-((5-(5-(1,3-dioxoisoindolin-2-yl)-1-pentyn-1-yl)-4-((4-fluorophenyl)amino)pyrimidin-2-yl)amino)benzonitrile (J14, 32 mg) as pale green solid.

후처리

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customThe organic layer was separated
  3. washwashed successively with 1.0 mol/L aqueous hydrochloric acid, saturated aqueous sodium hydrogencarbonate and saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. washThe obtained solid matter was washed with a mixed solvent of chloroform and methanol
  7. customdried under reduced pressure

출처 및 근거

ORD 기록
ord-7104e6fe1078445db38c6d9939ac438b
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09145415B2

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