Hydrochloric Acid → HCID 21192549, compound

HRID 1068016Notes

Reaction equation

HRID 1068016 reaction equation
[Cl:1][C:2]1[CH:31]=[CH:30][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]O)[CH:17]=3)[N:12]([CH2:23][CH2:24][O:25][CH2:26][CH2:27][O:28][CH3:29])[CH:11]=2)=[O:9])=[CH:4][CH:3]=1.N1C(C)=CC(C)=CC=1C.CS([Cl:45])(=O)=O.Cl>CN(C=O)C.CN(C1C=CN=CC=1)C.O>[Cl:1][C:2]1[CH:3]=[CH:4][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:45])[CH:17]=3)[N:12]([CH2:23][CH2:24][O:25][CH2:26][CH2:27][O:28][CH3:29])[CH:11]=2)=[O:9])=[CH:30][CH:31]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 79532,4,6-TrimethylpyridineHCID 31297Methanesulfonyl chlorideHCID 21192586HCID 21192586, compound

Product 1

HCID 21192549HCID 21192549, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of N-(4-chlorobenzyl)-6-(hydroxymethyl)-1-[2-(2-methoxyethoxy)ethyl]4-oxo-1,4-dihydro-3-quinolinecarboxamide (197 mg) from Preparation No. 41 in DMF (1 mL) is added 2,4,6-collidine (0.14 mL) and DMAP (8 mg). The solution is cooled to 0° C., and methanesulfonyl choride (69 μL) is added. After 18 h, the mixture is added to 20 mL of rapidly stirred water containing 0.75 mL of 1N HCl. The resulting precipitate is filtered, washed well with water, and dried in vacuo to afford 183 mg of N-(4-chlorobenzyl)-6-(chloromethyl)-1-[2-(2-methoxyethoxy)ethyl]4-oxo-1,4-dihydro-3-quinolinecarboxamide.

Workup

  1. filtrationThe resulting precipitate is filtered
  2. washwashed well with water
  3. customdried in vacuo

Sources & evidence

ORD record
ord-3d26294170fe490fa9d37042c0695f38
Source dataset
uspto-grants-2001_06
Patent number
US06248739B1

Reaction notes

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