Pyridine → 6-Trifluoromethyl-pyridine-3-sulfonic acid (5-trifluoromethyl-quinolin-8-yl)-amide

HRID 513493Notes

Reaction equation

HRID 513493 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:12]=[CH:11][C:10]([NH2:13])=[C:9]2[C:4]=1[CH:5]=[CH:6][CH:7]=[N:8]2.[F:16][C:17]([F:29])([F:28])[C:18]1[N:23]=[CH:22][C:21]([S:24](Cl)(=[O:26])=[O:25])=[CH:20][CH:19]=1.N1C=CC=CC=1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[F:15][C:2]([F:1])([F:14])[C:3]1[CH:12]=[CH:11][C:10]([NH:13][S:24]([C:21]2[CH:22]=[N:23][C:18]([C:17]([F:29])([F:16])[F:28])=[CH:19][CH:20]=2)(=[O:26])=[O:25])=[C:9]2[C:4]=1[CH:5]=[CH:6][CH:7]=[N:8]2

Participants

6

Reactant 3

HCID 1049PyridineHCID 103531188-Quinolinamine, 5-(trifluoromethyl)-2×HCID 455943116-(Trifluoromethyl)pyridine-3-sulfonyl chloride

Product 1

HCID 601641936-Trifluoromethyl-pyridine-3-sulfonic acid (5-trifluoromethyl-quinolin-8-yl)-amideYield 13%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

In a similar fashion using route 14 general procedure 27, 5-trifluoromethyl-quinolin-8-ylamine (Intermediate 45) (100 mg, 0.47 mmol), 6-(trifluoromethyl)pyridine-3-sulfonyl chloride (138 mg, 0.56 mmol), pyridine (0.08 ml, 0.94 mmol), DMAP (cat.) and DCM (5 ml) gave the title compound (25 mg, 13%) after purification by column chromatography with n-hexane/DCM (50:50) as the eluent.

Sources & evidence

ORD record
ord-a6758c5aaf494fababd9e0ff641c2435
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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