8-Aminoquinoline → 6-Trifluoromethyl-pyridine-3-sulfonic acid quinolin-8-ylamide

HRID 513464Notes

Reaction equation

HRID 513464 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]([F:25])([F:24])[C:14]1[N:19]=[CH:18][C:17]([S:20](Cl)(=[O:22])=[O:21])=[CH:16][CH:15]=1>CN(C1C=CN=CC=1)C>[N:10]1[C:11]2[C:6](=[CH:5][CH:4]=[CH:3][C:2]=2[NH:1][S:20]([C:17]2[CH:18]=[N:19][C:14]([C:13]([F:25])([F:12])[F:24])=[CH:15][CH:16]=2)(=[O:22])=[O:21])[CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 113598-AminoquinolineHCID 455943116-(Trifluoromethyl)pyridine-3-sulfonyl chloride

Product 1

HCID 681831946-Trifluoromethyl-pyridine-3-sulfonic acid quinolin-8-ylamideYield 58%

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

In a similar fashion using route 14 general procedure 27, 8-aminoquinoline (200 mg, 1.38 mmol), 6-(trifluoromethyl)pyridine-3-sulfonyl chloride (0.31 g, 1.25 mmol) and DMAP (cat) gave the title compound (250 mg, 58%) after purification by column chromatography with DCM as the eluent.

Sources & evidence

ORD record
ord-fe78b1c192e04fbaab44011a25af1c45
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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