8-Aminoquinoline → HCID 68183375, compound

HRID 513460Notes

Reaction equation

HRID 513460 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[C:14]([CH3:23])=[C:15]([S:19](Cl)(=[O:21])=[O:20])[CH:16]=[CH:17][CH:18]=1>CN(C1C=CN=CC=1)C>[F:12][C:13]1[C:14]([CH3:23])=[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 248204853-Fluoro-2-methylbenzene-1-sulfonyl chloride

Product 1

HCID 68183375HCID 68183375, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

In a similar fashion using route 14 general procedure 27, 8-aminoquinoline (100 mg, 0.69 mmol), 3-fluoro-2-methylbenzenesulfonyl chloride (210 mg, 1.04 mmol) and DMAP (cat.) gave the title compound (120 mg, 57%) after purification by column chromatography with DCM eluent.

Sources & evidence

ORD record
ord-625faaf30c4147968ac3cfb2b19f0c6d
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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