Pyridine → N-[[[1-(6-Fluoro-2-naphthalenylmethyl)-4-piperidinyl]amino]carbonyl]-6-quinoline carboxamide

HRID 868214Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 868214
[N:1]1[C:10]2[C:5](=[CH:6][C:7]([C:11](Cl)=[O:12])=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[F:14][C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][CH:24]=1)[CH:21]=[C:20]([CH2:25][N:26]1[CH2:31][CH2:30][CH:29]([NH:32][C:33]([NH2:35])=[O:34])[CH2:28][CH2:27]1)[CH:19]=[CH:18]2.N1C=CC=CC=1>ClCCCl>[F:14][C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][CH:24]=1)[CH:21]=[C:20]([CH2:25][N:26]1[CH2:27][CH2:28][CH:29]([NH:32][C:33]([NH:35][C:11]([C:7]3[CH:6]=[C:5]4[C:10](=[CH:9][CH:8]=3)[N:1]=[CH:2][CH:3]=[CH:4]4)=[O:12])=[O:34])[CH2:30][CH2:31]1)[CH:19]=[CH:18]2

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 12391963Quinoline-6-carbonyl chlorideHCID 21288076N-[[(6-fluoro-2-naphthalenyl)methyl]-4-piperidinyl]urea

Produkt 1

HCID 13853618N-[[[1-(6-Fluoro-2-naphthalenylmethyl)-4-piperidinyl]amino]carbonyl]-6-quinoline carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 111,2-DichloroethaneLösungsmittel

Versuchsvorschrift

A mixture of 6-quinolinoyl chloride (4.77 g, 22 mmol), N-[[(6-fluoro-2-naphthalenyl)methyl]-4-piperidinyl]urea (6.02 g, 20 mmol), dry pyridine (2.5 ml) and 1,2-dichloroethane (30 ml) is stirred at reflux for 18 hours. The solution is then cooled, washed with aqueous sodium carbonate solution, dried and evaporated. The residue is crystallised from ethanol to give the title compound, mp 200°-201° C. (softens, maleate salt).

Aufarbeitung

  1. temperatureat reflux for 18 hours
  2. temperatureThe solution is then cooled
  3. washwashed with aqueous sodium carbonate solution
  4. customdried
  5. customevaporated
  6. customThe residue is crystallised from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-fe4ffe43b4e3413780803c628c8a457f
Quelldatensatz
uspto-grants-1988_10
Patentnummer
US04778802

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