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

HRID 2266455Notes

Reaction equation

HRID 2266455 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.[C:39]1([S:45]([NH2:48])(=[O:47])=[O:46])[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1>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:48][S:45]([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)(=[O:47])=[O:46])=[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 7370BenzenesulfonamideHCID 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 57742498N-{2-[8-chloro-3-(4-chlorobenzyl)-2,4-dimethylquinolin-5-yloxy]acetyl}benzenesulfonamide

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

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), benzenesulfonamide (0.030 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 purified by column chromatography on silica gel, eluting with a mixture of methanol and dichloromethane (1:19 by volume), followed by trituration with cyclohexane containing a small amount of diethyl ether to afford title compound as a buff solid, 0.020 g.

Workup

  1. customThe mixture was purified by column chromatography on silica gel
  2. washeluting with a mixture of methanol and dichloromethane (1:19 by volume)

Sources & evidence

ORD record
ord-b1e8709a9ae84734b48b9409fd464c64
Source dataset
uspto-grants-2010_12
Patent number
US07858640B2

Reaction notes

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