8-Aminoquinoline → HCID 3838325, compound

HRID 513457Notes

Reaction equation

HRID 513457 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.[F:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[C:14]=1[S:20](Cl)(=[O:22])=[O:21]>CN(C1C=CN=CC=1)C>[F:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[C:14]=1[S:20]([NH: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)(=[O:22])=[O:21]

Participants

4

Reactant 2

HCID 113598-AminoquinolineHCID 27342712,6-Difluorobenzenesulfonyl chloride

Product 1

HCID 3838325HCID 3838325, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

In a similar fashion using route 14 general procedure 27, 8-aminoquinoline (100 mg, 0.70 mmol), 2,6-difluorobenzenesulfonyl chloride (170 mg, 0.83 mmol) and DMAP (cat.) gave the title compound (100 mg, 45%) after purification by column chromatography with DCM as the eluent followed by trituration from EtOAc/n-hexane.

Sources & evidence

ORD record
ord-d22172c18e6d4196b229261100d3ebfa
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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