Methanesulfonamide → N-{2-[8-chloro-3-(4-chlorobenzyl)-2,4-dimethylquinolin-5-yloxy]acetyl}methanesulfonamide

HRID 2266454Notes

Reaction equation

HRID 2266454 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:22][CH2:23][C:24]([OH:26])=O)=[C:6]2[C:11]=1[N:10]=[C:9]([CH3:12])[C:8]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=1)=[C:7]2[CH3:21].Cl.CN(C)CCCN=C=NCC.[CH3:39][S:40]([NH2:43])(=[O:42])=[O:41]>CN(C1C=CN=CC=1)C.ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:22][CH2:23][C:24]([NH:43][S:40]([CH3:39])(=[O:42])=[O:41])=[O:26])=[C:6]2[C:11]=1[N:10]=[C:9]([CH3:12])[C:8]([CH2:13][C:14]1[CH:15]=[CH:16][C:17]([Cl:20])=[CH:18][CH:19]=1)=[C:7]2[CH3:21]

Participants

6

Reactant 3

HCID 72879MethanesulfonamideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 57742525[8-chloro-3-(4-chlorobenzyl)-2,4-dimethylquinolin-5-yloxy]acetic Acid

Product 1

HCID 57742535N-{2-[8-chloro-3-(4-chlorobenzyl)-2,4-dimethylquinolin-5-yloxy]acetyl}methanesulfonamide

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A mixture of [8-chloro-3-(4-chlorobenzyl)-2,4-dimethylquinolin-5-yloxy]acetic acid (0.050 g), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.037 g), methanesulfonamide (0.020 g), and 4-(N,N-dimethylamino)pyridine (0.005 g) in dichloromethane (5.0 mL) was stirred at room temperature 1 hour. The mixture was diluted with dichloromethane and this solution was washed with water and then dried over magnesium sulfate. The solvent was removed under reduced pressure and purification of the residue by preparative reverse-phase HPLC using a gradient over 30 minutes of acetonitrile in water (40% to 95% of organic modifier) gave title compound as a yellow solid, 0.010 g

Workup

  1. washthis solution was washed with water
  2. dry with materialdried over magnesium sulfate
  3. customThe solvent was removed under reduced pressure and purification of the residue by preparative reverse-phase
  4. customover 30 minutes

Sources & evidence

ORD record
ord-1864e6892446482aa94c433f636414da
Source dataset
uspto-grants-2010_12
Patent number
US07858640B2

Reaction notes

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