Binap, (A+-)- → 1-(1-{4-[7-(1-Ethyl-propyl)-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino]-phenyl}-piperidin-4-yl)-ethanone

HRID 2189273ノート

反応式

HRID 2189273 の反応式
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12]N(C(=O)C)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[CH3:17][C:18]([O-:21])(C)[CH3:19].[Na+].Cl[C:24]1[N:25]=[CH:26][C:27]2[CH:32]=[CH:31][N:30]([CH:33]([CH2:36][CH3:37])[CH2:34][CH3:35])[C:28]=2[N:29]=1.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH2:34]([CH:33]([N:30]1[C:28]2[N:29]=[C:24]([NH:1][C:2]3[CH:3]=[CH:4][C:5]([N:8]4[CH2:9][CH2:10][CH:17]([C:18](=[O:21])[CH3:19])[CH2:12][CH2:13]4)=[CH:6][CH:7]=3)[N:25]=[CH:26][C:27]=2[CH:32]=[CH:31]1)[CH2:36][CH3:37])[CH3:35]

参加物

7

反応物 4

HCID 634876Binap, (A+-)-HCID 7362691-[4-(4-Aminophenyl)piperazin-1-yl]ethan-1-oneHCID 23676156Sodium t-butoxideHCID 580159322-Chloro-7-(pentan-3-yl)-7H-pyrrolo[2,3-d]pyrimidine

生成物 1

HCID 689530131-(1-{4-[7-(1-Ethyl-propyl)-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino]-phenyl}-piperidin-4-yl)-ethanone収率 80.5%

試薬・触媒・溶媒 2

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 312751,4-Dioxane溶媒2 回

反応条件

温度
100 °C

実験手順

To a mixture of 1-[4-(4-Amino-phenyl)-piperazin-1-yl]-ethanone (70.5 mg, 0.32 mmol) and NaOtBu (38.4 mg, 0.4 mmol) in 1,4-dioxane (0.3 mL) is added a solution of 2-Chloro-7-(1-ethyl-propyl)-7H-pyrrolo[2,3-d]pyrimidine (60 mg, 0.26 mmol) in 1,4-dioxane (0.6 mL) and a suspension of Pd2(dba)3 (12.2 mg, 0.013 mmol) and BINAP (16.6 mg, 0.026 mmol). The mixture is degassed, and heated at 100° C. for 3 hours. Then the mixture is cooled down to room temperature, diluted with EtOAc, and filtered through celite. The filtrate is concentrated under reduced pressure. The crude product is purified prep-HPLC to give 84.9 mg of the title compound as pale white solid.

後処理

  1. customThe mixture is degassed
  2. temperatureThen the mixture is cooled down to room temperature
  3. additiondiluted with EtOAc
  4. filtrationfiltered through celite
  5. concentrationThe filtrate is concentrated under reduced pressure
  6. customThe crude product is purified prep-HPLC

出典と根拠

ORDレコード
ord-c3c1c5dfc64347488b6e1e3f4d953ab8
出典データセット
uspto-grants-2012_12
特許番号
US08324225B2

反応ノート

読み込み中…