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

HRID 868214Notes

Reaction equation

HRID 868214 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-fe4ffe43b4e3413780803c628c8a457f
Source dataset
uspto-grants-1988_10
Patent number
US04778802

Reaction notes

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