Pyridine → Thiazole-2-sulfonic acid quinolin-8-ylamide

HRID 513491Notes

Reaction equation

HRID 513491 reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[S:6](Cl)(=[O:8])=[O:7].[N:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[N:10]1[C:15]2[C:14](=[CH:14][CH:13]=[CH:12][C:11]=2[NH:10][S:6]([C:2]2[S:1][CH:5]=[CH:4][N:3]=2)(=[O:8])=[O:7])[CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 2

HCID 1049PyridineHCID 115792352-Thiazolesulfonyl chloride2×

Product 1

HCID 60164190Thiazole-2-sulfonic acid quinolin-8-ylamideYield 15%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

In a similar fashion using route 14 general procedure 27, 8-aminoqunoline (250 mg, 1.73 mmol), thiazole-2-sulfonyl chloride (Intermediate 444) (413 mg, 2.25 mmol), pyridine (2 ml), DMAP (cat.) and DCM (2 ml) gave the title compound (110 mg, 15%), after purification by column chromatography with n-hexane/EtOAc (90:10) as the eluent.

Sources & evidence

ORD record
ord-de5cca23794446588dc120f00bf84346
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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