8-Aminoquinoline → HCID 68183385, compound

HRID 513444Notes

Reaction equation

HRID 513444 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.[CH3:12][O:13][C:14]1[CH:15]=[C:16]([S:20](Cl)(=[O:22])=[O:21])[CH:17]=[CH:18][CH:19]=1>CN(C1C=CN=CC=1)C>[CH3:12][O:13][C:14]1[CH:15]=[C:16]([S:20]([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:22])=[O:21])[CH:17]=[CH:18][CH:19]=1

Participants

4

Reactant 2

HCID 113598-AminoquinolineHCID 27375043-Methoxybenzenesulfonyl chloride

Product 1

HCID 68183385HCID 68183385, compoundYield 61.2%

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

In the similar fashion using route 14 general procedure 27, 8-aminoquinoline (200 mg, 1.38 mmol), 3-methoxybenzenesulfonyl chloride (260 mg, 1.3 mmol) and DMAP (cat.) gave the title compound (250 mg, 56%) after purification by column chromatography with DCM as the eluent.

Sources & evidence

ORD record
ord-5091b728e0ce4adb9d4332231abdcc7c
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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