6-Methoxy-8-quinolinamine → 4-chloro-2-fluoro-N-(6-methoxyquinolin-8-yl)benzenesulfonamide

HRID 513427Notes

Reaction equation

HRID 513427 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[C:11]([NH2:13])[CH:12]=1)[N:9]=[CH:8][CH:7]=[CH:6]2.[F:14][C:15]1[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:16]=1[S:22](Cl)(=[O:24])=[O:23]>>[Cl:21][C:19]1[CH:18]=[CH:17][C:16]([S:22]([NH:13][C:11]2[CH:12]=[C:3]([O:2][CH3:1])[CH:4]=[C:5]3[C:10]=2[N:9]=[CH:8][CH:7]=[CH:6]3)(=[O:23])=[O:24])=[C:15]([F:14])[CH:20]=1

Participants

3

Reactant 2

HCID 70236-Methoxy-8-quinolinamine2×HCID 27788604-Chloro-2-fluorobenzene-1-sulfonyl chloride

Product 1

HCID 601639234-chloro-2-fluoro-N-(6-methoxyquinolin-8-yl)benzenesulfonamideYield 56%

Procedure

In a similar fashion using route 14 general procedure 26, 6-methoxyquinolin-8-amine (Intermediate 23) (60 mg, 0.35 mmol), 2-fluoro-4-chlorobenzenesulfonyl chloride (100 mg, 0.45 mmol) gave the title compound (70 mg, 56%) after purification by column chromatography with DCM as the eluent.

Sources & evidence

ORD record
ord-927956a61f0c4fee8473d556af9add27
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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