4-Methoxybenzenesulfonyl chloride → HCID 4215345, compound

HRID 513438Notes

Reaction equation

HRID 513438 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2.[CH3:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([S:20](Cl)(=[O:22])=[O:21])=[CH:16][CH:15]=1>CN(C1C=CN=CC=1)C>[CH3:12][O:13][C:14]1[CH:15]=[CH:16][C:17]([S:20]([NH:1][C:2]2[CH:3]=[CH:4][CH:5]=[C:6]3[C:11]=2[N:10]=[CH:9][CH:8]=[CH:7]3)(=[O:22])=[O:21])=[CH:18][CH:19]=1

Participants

4

Reactant 2

HCID 74014-Methoxybenzenesulfonyl chlorideHCID 113598-Aminoquinoline

Product 1

HCID 4215345HCID 4215345, compoundYield 61.2%

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

In the similar fashion using route 14 general procedure 27, 8-aminoquinoline (200 mg, 1.38 mmol), 4-methoxybenzenesulfonyl chloride (300 mg, 1.3 mmol) and DMAP (cat.) gave the title compound (250 mg, 58%) after purification by column chromatography with DCM/MeOH/NH3 (100-100:1:1 drop).

Sources & evidence

ORD record
ord-1359da30d2bd410ca50da8065602f942
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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