Pyridine → 6-Trifluoromethyl-pyridine-3-sulfonic acid (6-fluoro-quinolin-8-yl)-amide

HRID 513486Notes

Reaction equation

HRID 513486 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.[F:13][C:14]([F:26])([F:25])[C:15]1[N:20]=[CH:19][C:18]([S:21](Cl)(=[O:23])=[O:22])=[CH:17][CH:16]=1.N1C=CC=CC=1>C(Cl)Cl.CN(C1C=CN=CC=1)C>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([NH:12][S:21]([C:18]3[CH:19]=[N:20][C:15]([C:14]([F:26])([F:13])[F:25])=[CH:16][CH:17]=3)(=[O:23])=[O:22])[CH:11]=1)[N:8]=[CH:7][CH:6]=[CH:5]2

Participants

6

Reactant 3

HCID 1049PyridineHCID 132279926-Fluoroquinolin-8-amine2×HCID 455943116-(Trifluoromethyl)pyridine-3-sulfonyl chloride

Product 1

HCID 601641896-Trifluoromethyl-pyridine-3-sulfonic acid (6-fluoro-quinolin-8-yl)-amideYield 26.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

In a similar fashion using route 14 general procedure 27, 6-fluoroquinolin-8-ylamine (Intermediate 48) (150 mg, 0.92 mmol), 6-(trifluoromethyl)pyridine-3-sulfonyl chloride (250 mg, 1.01 mmol) in DCM (2 ml), DMAP (cat), pyridine (146 mg, 1.84 mmol) and DCM (5 ml) gave the title compound (90 mg, 26%) after purification by column chromatography with n-hexane/EtOAc (90:10) as the eluent.

Sources & evidence

ORD record
ord-2b98fa839d7e4d83a2e86d2e1b803c59
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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