Benzenesulfonyl chloride → N-(5,6-Dimethyl-quinolin-8-yl)-benzenesulfonamide

HRID 513482Notes

Reaction equation

HRID 513482 reaction equation
[CH3:1][C:2]1[C:11]([CH3:12])=[CH:10][C:9]([NH2:13])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.[C:14]1([S:20](Cl)(=[O:22])=[O:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CN(C1C=CN=CC=1)C>[CH3:1][C:2]1[C:11]([CH3:12])=[CH:10][C:9]([NH:13][S:20]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)(=[O:22])=[O:21])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2

Participants

4

Reactant 2

HCID 7369Benzenesulfonyl chlorideHCID 1104658-Quinolinamine, 5,6-dimethyl-2×

Product 1

HCID 68183094N-(5,6-Dimethyl-quinolin-8-yl)-benzenesulfonamideYield 10%

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

In a similar fashion using route 14 general procedure 27, 5,6-dimethylquinolin-8-amine (Intermediate 55) (60 mg, 0.38 mmol), benzenesulfonyl chloride (72 mg, 0.41 mmol) and DMAP (cat.) gave the title compound (10 mg, 10%) after purification by column chromatography with DCM as the eluent.

Sources & evidence

ORD record
ord-893bf035e9c143b9ad62ba861d2ccc05
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

Loading…