Tributylphosphine → 3-Chloro-4-fluorophenylamino-N-{2-methyl-5-[3-(4methylpiperazin-1yl)-propoxyl]phenyl}acetamide

HRID 1267924Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1267924
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][CH2:10][C:11]([NH:13][C:14]2[CH:19]=[C:18]([OH:20])[CH:17]=[CH:16][C:15]=2[CH3:21])=[O:12])[CH:5]=[CH:6][C:7]=1[F:8].[CH3:22][N:23]1[CH2:28][CH2:27][N:26]([CH2:29][CH2:30][CH2:31]O)[CH2:25][CH2:24]1.C(P(CCCC)CCCC)CCC.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>O1CCCC1.C(OCC)C>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][CH2:10][C:11]([NH:13][C:14]2[CH:19]=[C:18]([O:20][CH2:31][CH2:30][CH2:29][N:26]3[CH2:27][CH2:28][N:23]([CH3:22])[CH2:24][CH2:25]3)[CH:17]=[CH:16][C:15]=2[CH3:21])=[O:12])[CH:5]=[CH:6][C:7]=1[F:8]

Komponenten

7

Edukt 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 792083-(4-Methyl-1-piperazine)propan-1-olHCID 185423932-(3-chloro-4-fluoro-phenylamino)-N-(5-hydroxy-2-methyl-phenyl)-acetamide

Produkt 1

HCID 98037383-Chloro-4-fluorophenylamino-N-{2-methyl-5-[3-(4methylpiperazin-1yl)-propoxyl]phenyl}acetamideAusbeute 57,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 2-(3-chloro-4-fluoro-phenylamino)-N-(5-hydroxy-2-methyl-phenyl)-acetamide (0.400 g) and 4-methyl-1-piperazinepropanol (0.270 g) in tetrahydrofuran (20 ml) under a nitrogen atmosphere was added tributylphosphine (0.64 ml) and 1,1′-(azodicarbonyl)dipiperidine (0.656 g) and the mixture stirred at ambient temperature for 20 hours. The reaction mixture was poured into diethylether and filtered through Celite. After concentration, the residue was purified by NPHPLC (eluting with 75% ethanol in dichloromethane) to afford the title compound (0.334 g).

Aufarbeitung

  1. filtrationfiltered through Celite
  2. concentrationAfter concentration
  3. customthe residue was purified by NPHPLC (eluting with 75% ethanol in dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-69be2603638b43f9957102d23f707a93
Quelldatensatz
uspto-grants-2003_04
Patentnummer
US06555541B1

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