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

HRID 2189273Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2189273
[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]

Komponenten

7

Edukt 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

Produkt 1

HCID 689530131-(1-{4-[7-(1-Ethyl-propyl)-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino]-phenyl}-piperidin-4-yl)-ethanoneAusbeute 80,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 312751,4-DioxaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-c3c1c5dfc64347488b6e1e3f4d953ab8
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08324225B2

Notizen zur Reaktion

Wird geladen…