8-Aminoquinoline → HCID 68183273, compound

HRID 513455Notes

Reaction equation

HRID 513455 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:12][C:13]1[C:14]([F:23])=[C:15]([S:19](Cl)(=[O:21])=[O:20])[CH:16]=[CH:17][CH:18]=1>CN(C1C=CN=CC=1)C>[Cl:12][C:13]1[C:14]([F:23])=[C:15]([S:19]([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:21])=[O:20])[CH:16]=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 113598-AminoquinolineHCID 27783213-Chloro-2-fluorobenzenesulfonyl Chloride

Product 1

HCID 68183273HCID 68183273, compoundYield 35%

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), 3-chloro-2-fluorobenzenesulfonyl chloride (180 mg, 0.83 mmol) and DMAP (cat.) gave the title compound (80 mg, 35%) after purification by column chromatography with DCM as the eluent followed by trituration from EtOAc/n-hexane.

Sources & evidence

ORD record
ord-9eb76d2b37db481197289f5af0568605
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

Loading…