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

HRID 2189273노트

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HRID 2189273 반응식
[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]

참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 312751,4-Dioxane용매2회

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온도
100 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-c3c1c5dfc64347488b6e1e3f4d953ab8
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08324225B2

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