Pyridine → HCID 22010872, Verbindung

HRID 323159Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 323159
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:14]([NH:16][C:17]3[CH:39]=[CH:38][C:20]([C:21]([N:23]([CH3:37])[C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[O:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][NH2:36])=[O:22])=[CH:19][CH:18]=3)=[O:15])=[CH:10][CH:11]=[CH:12][CH:13]=2)=[CH:4][CH:3]=1.N1C=CC=CC=1.Cl[C:47]([O:49][C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1)=[O:48]>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]([CH3:37])[C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[O:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][NH:36][C:47]([O:49][C:50]4[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=4)=[O:48])=[O:22])=[CH:38][CH:39]=3)=[O:15])=[CH:10][CH:11]=[CH:12][CH:13]=2)=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 15891Phenyl chloroformateHCID 22011014HCID 22011014, Verbindung

Produkt 1

HCID 22010872HCID 22010872, VerbindungAusbeute 63,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of 4-(4′-methylbiphenyl-2-carboxamido)-N-methyl-N-[2-(5-aminopentyloxy)phenyl]benzamide (750 mg) in dichloromethane (30 ml) was treated with pyridine (681 mg) and phenyl chloroformate (675 mg). After 18 hours, the solvent was removed and the residue was dissolved in ethyl acetate, washed with 1N hydrochloric acid, water, saturated sodium hydrogen carbonate solution and brine, dried over sodium sulfate, concentrated, and purified by silica gel column chromatography (SiO2; 50 g, 1% methanol in dichloromethane) to give 4-(4′-methylbiphenyl-2-carboxamido)-N-methyl-N-[2-(5-phenoxycarbonylaminopentyloxy)phenyl]benzamide (590 mg).

Aufarbeitung

  1. customthe solvent was removed
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washwashed with 1N hydrochloric acid, water, saturated sodium hydrogen carbonate solution and brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. custompurified by silica gel column chromatography (SiO2; 50 g, 1% methanol in dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-d27eb74558dc4befbb3fe684d1d6c392
Quelldatensatz
uspto-grants-2001_04
Patentnummer
US06211242B1

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