Water → N-[(4-chlorophenyl)methyl]-6-[(4,4-difluoro-1-piperidyl)methyl]-1-methyl-4-oxo-quinoline-3-carboxamide

HRID 1067995

Reaction equation

HRID 1067995 reaction equation
[Cl:1][C:2]1[CH:25]=[CH:24][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:19](=[O:20])[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([CH2:21]Cl)[CH:17]=3)[N:12]([CH3:23])[CH:11]=2)=[O:9])=[CH:4][CH:3]=1.C(N(CC)C(C)C)(C)C.[F:35][C:36]1([F:42])[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]1.O>CN1CCCC1=O>[Cl:1][C:2]1[CH:25]=[CH:24][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:19](=[O:20])[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([CH2:21][N:39]4[CH2:40][CH2:41][C:36]([F:42])([F:35])[CH2:37][CH2:38]4)[CH:17]=3)[N:12]([CH3:23])[CH:11]=2)=[O:9])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 27583524,4-DifluoropiperidineHCID 21192571N-(4-Chlorobenzyl)-6-(chloromethyl)-1-methyl-4-oxo-1,4-dihydro-3-quinolinecarboxamide

Product 1

HCID 16073868N-[(4-chlorophenyl)methyl]-6-[(4,4-difluoro-1-piperidyl)methyl]-1-methyl-4-oxo-quinoline-3-carboxamideYield 84%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To a solution of N-(4-chlorobenzyl)-6-(chloromethyl)-1-methyl-4-oxo-1,4-dihydro-3-quinolinecarboxamide from Preparation No. 35 (50 mg) in 1-methyl-2-pyrrolidinone (3 mL) is added N,N-diisopropylethylamine (0.03 mL) and 4,4-difluoropiperidine from Preparation No. 37 (50 mg). The reaction mixture is stirred at room temperature overnight and then heated at 50° C. for 4 hrs. The mixture is cooled to room temperature and poured into water to precipitate the product. The crude solid is recrystallized from CH2Cl2/hexanes to afford 51.5 mg (84%) of the title compound as a white solid.

Workup

  1. customfrom Preparation No
  2. temperatureheated at 50° C. for 4 hrs
  3. temperatureThe mixture is cooled to room temperature
  4. customto precipitate the product
  5. customThe crude solid is recrystallized from CH2Cl2/hexanes

Sources & evidence

ORD record
ord-aedcdc7c47ad4746a4a3cedbbfbe1bf4
Source dataset
uspto-grants-2001_06
Patent number
US06248739B1

Linked notes

Loading…