Pyridine-3-sulfonyl chloride → Pyridine-3-sulfonic acid (6-fluoro-quinolin-8-yl)-amide

HRID 513476Notes

Reaction equation

HRID 513476 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([NH2:12])[CH:11]=1)[N:8]=[CH:7][CH:6]=[CH:5]2.[N:13]1[CH:18]=[CH:17][CH:16]=[C:15]([S:19](Cl)(=[O:21])=[O:20])[CH:14]=1>CN(C1C=CN=CC=1)C>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([NH:12][S:19]([C:15]3[CH:14]=[N:13][CH:18]=[CH:17][CH:16]=3)(=[O:21])=[O:20])[CH:11]=1)[N:8]=[CH:7][CH:6]=[CH:5]2

Participants

4

Reactant 2

HCID 3164136Pyridine-3-sulfonyl chloride2×HCID 132279926-Fluoroquinolin-8-amine2×

Product 1

HCID 68190277Pyridine-3-sulfonic acid (6-fluoro-quinolin-8-yl)-amideYield 32%

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

In a similar fashion using route 14 general procedure 27, 6-fluoroquinolin-8-amine (Intermediate 48) (100 mg, 0.62 mmol), pyridine 3-sulfonyl chloride (Intermediate 17) (130 mg, 0.74 mmol) and DMAP (cat.) gave the title compound (60 mg, 32%) after purification by column chromatography with n-hexane/DCM (1:0-0:1) gradient elution followed by recrystallisation from DCM/n-pentane.

Sources & evidence

ORD record
ord-94d81bddf56844818be10c2c84de5ff7
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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