Cesium carbonate → 1-[4-[2-(Isoquinolin-3-ylamino)-pyridin-4-ylmethyl]-piperazin-1-yl]-ethanone

HRID 1257126

Reaktionsgleichung

Reaktionsgleichung von HRID 1257126
Cl[C:2]1[CH:7]=[C:6]([CH2:8][N:9]2[CH2:14][CH2:13][N:12]([C:15](=[O:17])[CH3:16])[CH2:11][CH2:10]2)[CH:5]=[CH:4][N:3]=1.[NH2:18][C:19]1[N:20]=[CH:21][C:22]2[C:27]([CH:28]=1)=[CH:26][CH:25]=[CH:24][CH:23]=2.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.C([O-])([O-])=O.[Cs+].[Cs+]>C1(C)C=CC=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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].CCOC(C)=O>[CH:21]1[C:22]2[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:28]=[C:19]([NH:18][C:2]2[CH:7]=[C:6]([CH2:8][N:9]3[CH2:14][CH2:13][N:12]([C:15](=[O:17])[CH3:16])[CH2:11][CH2:10]3)[CH:5]=[CH:4][N:3]=2)[N:20]=1

Komponenten

8

Edukt 4

HCID 10796Cesium carbonateHCID 311869Isoquinolin-3-AmineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 58285182HCID 58285182, Verbindung

Produkt 1

HCID 446124701-[4-[2-(Isoquinolin-3-ylamino)-pyridin-4-ylmethyl]-piperazin-1-yl]-ethanone

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

1-(2-Chloropyridin-4-ylmethyl)-4-acetylpiperazine (1.0 equiv) (Preparation B-15) was mixed with 3-aminoisoquinoline (1.0 equiv), Pd2(dba)3(0.1 equiv), xantphos (0.15 equiv), and Cs2CO3 (1.4 equiv) in toluene. The mixture was refluxed overnight, and EtOAc was added in to dilute the mixture. After filtration, the filtrate was concentrated and applied onto a silica gel column. The title compound was obtained as a yellow solid (50 mg, yield 48%). 1H NMR (CDCl3, 300 MHz) δ: 2.10 (s, 3H, Ac), 2.47 (t, J=4.1 Hz, 4H, PyCH2NCH2CH2), 3.58 (dt, J=4.8 Hz, 50.7 Hz, 4H, NCH2CO), 3.60 (s, 2H, pyridylCH2), 6.86-8.99 (m, 9H, isoquinolyl+pyridyl).

Aufarbeitung

  1. temperatureThe mixture was refluxed overnight
  2. additionto dilute the mixture
  3. filtrationAfter filtration
  4. concentrationthe filtrate was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-4e4cae14340f4d6fb08ae527b6bbb156
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08461339B2

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