Pyridine → Pyridine-2-sulfonic acid (6-fluoro-quinolin-8-yl)-amide

HRID 513496Notes

Reaction equation

HRID 513496 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]=[CH:15][C:14]=1[S:19](Cl)(=[O:21])=[O:20].N1C=CC=CC=1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([NH:12][S:19]([C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][N:13]=3)(=[O:21])=[O:20])[CH:11]=1)[N:8]=[CH:7][CH:6]=[CH:5]2

Participants

6

Reactant 3

HCID 1049PyridineHCID 3787675Pyridine-2-sulfonyl ChlorideHCID 132279926-Fluoroquinolin-8-amine2×

Product 1

HCID 60164303Pyridine-2-sulfonic acid (6-fluoro-quinolin-8-yl)-amideYield 43%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

In a similar fashion using route 14 general procedure 27, 6-fluoroquinolin-8-ylamine (Intermediate 48) (125 mg, 0.77 mmol), pyridine-2-sulfonyl chloride Intermediate 18) (163 mg, 0.92 mmol), pyridine (0.12 ml, 1.54 mmol), DMAP (cat.) and DCM (5 ml) gave the title compound (100 mg, 43%) after purification by column chromatography with n-hexane/DCM (50:50) as the eluent.

Sources & evidence

ORD record
ord-fd70109bb6904d6eb960865438e7fc94
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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