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

HRID 513492Notes

Reaction equation

HRID 513492 reaction equation
[F:1][C:2]([F:16])([F:15])[O:3][C:4]1[CH:5]=[C:6]2[C:11](=[C:12]([NH2:14])[CH:13]=1)[N:10]=[CH:9][CH:8]=[CH:7]2.[F:17][C:18]([F:30])([F:29])[C:19]1[N:24]=[CH:23][C:22]([S:25](Cl)(=[O:27])=[O:26])=[CH:21][CH:20]=1.N1C=CC=CC=1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[F:16][C:2]([F:1])([F:15])[O:3][C:4]1[CH:5]=[C:6]2[C:11](=[C:12]([NH:14][S:25]([C:22]3[CH:23]=[N:24][C:19]([C:18]([F:30])([F:17])[F:29])=[CH:20][CH:21]=3)(=[O:27])=[O:26])[CH:13]=1)[N:10]=[CH:9][CH:8]=[CH:7]2

Participants

6

Reactant 3

HCID 1049PyridineHCID 455943116-(Trifluoromethyl)pyridine-3-sulfonyl chlorideHCID 681830016-(Trifluoromethoxy)quinolin-8-amine2×

Product 1

HCID 601641926-Trifluoromethyl-pyridine-3-sulfonic acid (6-trifluoromethoxy-quinolin-8-yl)-amideYield 42.9%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

In a similar fashion using route 14 general procedure 27, 6-trifluoromethoxy-quinolin-8-ylamine (Intermediate 46) (75 mg, 0.32 mmol), 6-(trifluoromethyl)pyridine-3-sulfonyl chloride (96 mg, 0.39 mmol), DMAP (cat.), pyridine (0.05 ml, 0.65 mmol) and DCM (2 ml) gave the title compound (60 mg, 42%) after purification by column chromatography with n-hexane/EtOAc (90:10) as the eluent.

Sources & evidence

ORD record
ord-0b006ee69deb445fafad0e141b5a9790
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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