Pyridine → HCID 22010636, Verbindung

HRID 323161Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 323161
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:14]([NH:16][C:17]3[CH:37]=[CH:36][C:20]([C:21]([N:23]([CH3:35])[C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[O:30][CH2:31][CH2:32][CH2:33][OH:34])=[O:22])=[CH:19][CH:18]=3)=[O:15])=[CH:10][CH:11]=[CH:12][CH:13]=2)=[CH:4][CH:3]=1.[N:38]1[CH:43]=[CH:42]C=[CH:40][CH:39]=1.Cl[C:45](OC1C=CC([N+]([O-])=O)=CC=1)=[O:46].[CH3:57][N:58]1CCNCC1>ClCCl>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:9]([C:14]([NH:16][C:17]3[CH:18]=[CH:19][C:20]([C:21]([N:23]([CH3:35])[C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[O:30][CH2:31][CH2:32][CH2:33][O:34][C:45]([N:38]4[CH2:39][CH2:40][N:58]([CH3:57])[CH2:42][CH2:43]4)=[O:46])=[O:22])=[CH:36][CH:37]=3)=[O:15])=[CH:10][CH:11]=[CH:12][CH:13]=2)=[CH:6][CH:7]=1

Komponenten

6

Edukt 4

HCID 1049PyridineHCID 531671-MethylpiperazineHCID 821294-Nitrophenyl chloroformateHCID 22010692HCID 22010692, Verbindung

Produkt 1

HCID 22010636HCID 22010636, VerbindungAusbeute 53,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of 4-(4′-methylbiphenyl-2-carboxamido)-N-methyl-N-[2-(3-hydroxypropoxy)phenyl]benzamide (300 mg) in dichloromethane (15 ml) was treated with pyridine (95.8 mg) and p-nitrophenyl chloroformate (183 mg). After 4.5 hours, 1-methylpiperazine (303 mg) was added to the reaction mixture and stirred for a further 1 hour at ambient temperature. After concentration, the residue was dissolved in ethyl acetate and washed with saturated sodium hydrogen carbonate solution and brine, dried over sodium sulfate, concentrated, and purified by silica gel column chromatography (SiO2; 30 g, 3% methanol in dichloromethane) to give 4-(4′-methylbiphenyl-2-carboxamido)-N-methyl-N-[2-[3-(4-methylpiperazin-1-carbonyloxy)propoxy]phenyl]benzamide (200 mg) as white amorphous.

Aufarbeitung

  1. concentrationAfter concentration
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washwashed with saturated sodium hydrogen carbonate solution and brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. custompurified by silica gel column chromatography (SiO2; 30 g, 3% methanol in dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-0cb9e8ba924b448686f85f3acd3001bf
Quelldatensatz
uspto-grants-2001_04
Patentnummer
US06211242B1

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