Water → N-(4-Chlorobenzyl)-1-methyl-4-oxo-6-(4-thiomorpholinyl-methyl)-1,4-dihydro-3-quinolinecarboxamide

HRID 1067264

Reaction equation

HRID 1067264 reaction equation
[CH3:1][S:2](Cl)(=O)=O.[Cl:6][C:7]1[CH:30]=[CH:29][C:10]([CH2:11][NH:12][C:13]([C:15]2[C:24](=[O:25])[C:23]3[C:18](=[CH:19][CH:20]=[C:21]([CH2:26]O)[CH:22]=3)[N:17]([CH3:28])[CH:16]=2)=[O:14])=[CH:9][CH:8]=1.[N:31]1[C:36](C)=CC(C)=[CH:33][C:32]=1C.O>CN(C1C=CN=CC=1)C.CN(C=O)C>[Cl:6][C:7]1[CH:30]=[CH:29][C:10]([CH2:11][NH:12][C:13]([C:15]2[C:24](=[O:25])[C:23]3[C:18](=[CH:19][CH:20]=[C:21]([CH2:26][N:31]4[CH2:36][CH2:1][S:2][CH2:33][CH2:32]4)[CH:22]=3)[N:17]([CH3:28])[CH:16]=2)=[O:14])=[CH:9][CH:8]=1

Participants

7

Reactant 4

HCID 962WaterHCID 79532,4,6-TrimethylpyridineHCID 31297Methanesulfonyl chlorideHCID 15516933N-(4-Chlorobenzyl)-6-(hydroxymethyl)-1-methyl-4-oxo-1,4-dihydro-3-quinolinecarboxamide

Product 1

HCID 15516934N-(4-Chlorobenzyl)-1-methyl-4-oxo-6-(4-thiomorpholinyl-methyl)-1,4-dihydro-3-quinolinecarboxamideYield 74%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

Methanesulfonyl chloride (0.193 mL) is added to a solution of N-(4-chloro-benzyl)-6-(hydroxymethyl)-1-methyl-4-oxo-1,4-dihydro-3-quinolinecarboxamide (357 mg) from Example No. 2, DMAP (20 mg), and 2,4,6-collidine (0.33 mL) in anhydrous DMF (20 mL). The mixture is stirred at room temperate for 2 h, and poured into water (60 mL). The resulting percipitate is filtered, washed with water (20 mL), and recrystallized from acetonitrile to afford 0.328 g (74%) of the title compound as a white solid.

Workup

  1. filtrationThe resulting percipitate is filtered
  2. washwashed with water (20 mL)
  3. customrecrystallized from acetonitrile

Sources & evidence

ORD record
ord-894f43e873d8468f8926918e183d7075
Source dataset
uspto-grants-2001_06
Patent number
US06248736B1

Linked notes

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