6-Methoxy-8-quinolinamine → N-(6-methoxyquinolin-8-yl)benzenesulfonamide

HRID 513467Notes

Reaction equation

HRID 513467 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[C:11]([NH2:13])[CH:12]=1)[N:9]=[CH:8][CH:7]=[CH:6]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][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[C:11]([NH:13][S:20]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)(=[O:22])=[O:21])[CH:12]=1)[N:9]=[CH:8][CH:7]=[CH:6]2

Participants

4

Reactant 2

HCID 70236-Methoxy-8-quinolinamine2×HCID 7369Benzenesulfonyl chloride

Product 1

HCID 821430N-(6-methoxyquinolin-8-yl)benzenesulfonamideYield 63.6%

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

In the similar fashion using route 14 general procedure 27, 6-methoxyquinolin-8-amine (Intermediate 23) (250 mg, 1.43 mmol), benzenesulfonyl chloride (220 μl, 1.3 mmol) and DMAP (cat.) gave the title compound (260 mg, 57%) after purification by column chromatography with DCM as the eluent.

Sources & evidence

ORD record
ord-ce87dcc548354721babfa6a555306cf7
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

Loading…