1-Methylpiperazine → 4-[(7-chloro-4-methyl-1H-indol-5-yl)amino]-5-{4-[2-(4-methylpiperazin-1-yl)ethoxy]phenyl}nicotinonitrile

HRID 506208Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 506208
Cl[CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:12]=[N:13][CH:14]=[C:15]([C:18]=2[NH:19][C:20]2[C:21]([CH3:30])=[C:22]3[C:26](=[C:27]([Cl:29])[CH:28]=2)[NH:25][CH:24]=[CH:23]3)[C:16]#[N:17])=[CH:7][CH:6]=1.[CH3:31][N:32]1[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]1>COCCOC>[Cl:29][C:27]1[CH:28]=[C:20]([NH:19][C:18]2[C:15]([C:16]#[N:17])=[CH:14][N:13]=[CH:12][C:11]=2[C:8]2[CH:7]=[CH:6][C:5]([O:4][CH2:3][CH2:2][N:35]3[CH2:36][CH2:37][N:32]([CH3:31])[CH2:33][CH2:34]3)=[CH:10][CH:9]=2)[C:21]([CH3:30])=[C:22]2[C:26]=1[NH:25][CH:24]=[CH:23]2

Komponenten

4

Edukt 2

HCID 531671-MethylpiperazineHCID 684656455-[4-(2-chloroethoxy)phenyl]-4-[(7-chloro-4-methyl-1H-indol-5-yl)amino]nicotinonitrile

Produkt 1

HCID 684675104-[(7-chloro-4-methyl-1H-indol-5-yl)amino]-5-{4-[2-(4-methylpiperazin-1-yl)ethoxy]phenyl}nicotinonitrileAusbeute 93,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

A solution of 5-[4-(2-chloroethoxy)phenyl]-4-[(7-chloro-4-methyl-1H-indol-5-yl)amino]nicotinonitrile (144 mg, 0.3 mmol) and 1-methylpiperazine (330 mg, 3.3 mmol) in DME (3 mL) was stirred at 110° C. for 48 h. After the solution was concentrated, 1 N HCl was added and the aqueous phase was extracted with ethyl acetate, adjusted to pH of 10 by adding sodium carbonate, and extracted with ethyl acetate. The combined organic phases were washed with water and brine, dried over magnesium sulfate, and concentrated to give 4-[(7-chloro-4-methyl-1H-indol-5-yl)amino]-5-{4-[2-(4-methylpiperazin-1-yl)ethoxy]phenyl}nicotinonitrile as a yellow solid (140 mg, 84% yield). HPLC retention time: 5.1 min.(g); MS: 501.3 (M+H); and HRMS: 501.2159.

Aufarbeitung

  1. concentrationAfter the solution was concentrated
  2. addition1 N HCl was added
  3. extractionthe aqueous phase was extracted with ethyl acetate
  4. additionby adding sodium carbonate
  5. extractionextracted with ethyl acetate
  6. washThe combined organic phases were washed with water and brine
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-cd07c1abc92748d784e60e92316011db
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07781591B2

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