Water → N-(4-chlorobenzyl)-8-fluoro-1-methyl-6-(4-morpholinylmethyl)-4-oxo-1,4-dihydro-3-quinolinecarboxamide

HRID 1067265Notes

Reaction equation

HRID 1067265 reaction equation
[Cl:1][C:2]1[CH:30]=[CH:29][C:5]([CH2:6][NH:7][C:8]([C:10]2[CH:11]=[N:12][C:13]3[C:18]([C:19]=2[OH:20])=[CH:17][C:16]([CH2:21][N:22]2[CH2:27][CH2:26][O:25][CH2:24][CH2:23]2)=[CH:15][C:14]=3[F:28])=[O:9])=[CH:4][CH:3]=1.[C:31]([O-])([O-])=O.[K+].[K+].CI.O>CN(C=O)C>[Cl:1][C:2]1[CH:30]=[CH:29][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:19](=[O:20])[C:18]3[C:13](=[C:14]([F:28])[CH:15]=[C:16]([CH2:21][N:22]4[CH2:27][CH2:26][O:25][CH2:24][CH2:23]4)[CH:17]=3)[N:12]([CH3:31])[CH:11]=2)=[O:9])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178522914HCID 178522914, compound

Product 1

HCID 9911299N-(4-chlorobenzyl)-8-fluoro-1-methyl-6-(4-morpholinylmethyl)-4-oxo-1,4-dihydro-3-quinolinecarboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N-(4-chlorobenzyl)-8-fluoro-4-hydroxy-6-(4-morpholinylmethyl)-3-quinolinecarboxamide, (can be prepared according to the procedure described in PCT patent application, W099/32450) (147 mg) in anhydrous DMF (3 mL) is added K2CO3 (71.2 mg) followed by CH3I (0.026 mL). The reaction mixture is stirred at room temperature for 30 min, then poured into H2O (40 mL) to precipitate the product. The solid is collected, adsorbed onto silica, and chromatographed (1% MeOH in CH2Cl2 (2L)). Fractions homogenous by TLC are combined and concentrated to afford 55.3 mg of the title compound as a white solid.

Workup

  1. customto precipitate the product
  2. customThe solid is collected
  3. customchromatographed (1% MeOH in CH2Cl2 (2L))
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-08d4ee58617144af92d5be7d2fe9e9a7
Source dataset
uspto-grants-2001_06
Patent number
US06248736B1

Reaction notes

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