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

HRID 2266454Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2266454
[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]

Komponenten

6

Edukt 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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

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

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-1864e6892446482aa94c433f636414da
Quelldatensatz
uspto-grants-2010_12
Patentnummer
US07858640B2

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