8-Aminoquinoline → 3-(Quinolin-8-ylsulfamoyl)-benzoic acid methyl ester

HRID 513450

Reaction equation

HRID 513450 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.Cl[S:13]([C:16]1[CH:17]=[C:18]([CH:23]=[CH:24][CH:25]=1)[C:19]([O:21][CH3:22])=[O:20])(=[O:15])=[O:14]>CN(C1C=CN=CC=1)C>[CH3:22][O:21][C:19](=[O:20])[C:18]1[CH:23]=[CH:24][CH:25]=[C:16]([S:13](=[O:14])(=[O:15])[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)[CH:17]=1

Participants

4

Reactant 2

HCID 113598-AminoquinolineHCID 113339Benzoic acid, 3-(chlorosulfonyl)-, methyl ester

Product 1

HCID 317029933-(Quinolin-8-ylsulfamoyl)-benzoic acid methyl esterYield 64%

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

In the similar fashion using route 14 general procedure 27, 8-aminoquinoline (100 mg, 0.69 mmol), methyl 3-chlorosulfonylbenzoate (160 mg, 0.69 mmol) and DMAP (cat.) gave the title compound (150 mg, 64%) after purification by column chromatography with DCM as the eluent.

Sources & evidence

ORD record
ord-8dee330c2dd447c49a029927665986ad
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Linked notes

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