8-Aminoquinoline → HCID 8823684, compound

HRID 513449Notes

Reaction equation

HRID 513449 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[S:13]([C:16]1[CH:25]=[CH:24][CH:23]=[CH:22][C:17]=1[C:18]([O:20][CH3:21])=[O:19])(=[O:15])=[O:14]>CN(C1C=CN=CC=1)C>[CH3:21][O:20][C:18](=[O:19])[C:17]1[CH:22]=[CH:23][CH:24]=[CH:25][C:16]=1[S:13](=[O:14])(=[O:15])[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

Participants

4

Reactant 2

HCID 113598-AminoquinolineHCID 117830Benzoic acid, 2-(chlorosulfonyl)-, methyl ester

Product 1

HCID 8823684HCID 8823684, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

In the similar fashion using route 14 general procedure 27, 8-aminoquinoline (100 mg, 0.69 mmol), methyl 2-chlorosulfonylbenzoate (160 mg, 0.69 mmol) and DMAP (cat.) gave the title compound (80 mg, 35%) after purification by column chromatography with DCM as the eluent.

Sources & evidence

ORD record
ord-077170efd6524e69812e822e9678fa0c
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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