Pyridine → Pyridine-2-sulfonic acid (5-trifluoromethyl-quinolin-8-yl)-amide

HRID 513494

Reaction equation

HRID 513494 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.[N:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[S:22](Cl)(=[O:24])=[O:23].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:22]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][N:16]=2)(=[O:24])=[O:23])=[C:9]2[C:4]=1[CH:5]=[CH:6][CH:7]=[N:8]2

Participants

6

Reactant 3

HCID 1049PyridineHCID 3787675Pyridine-2-sulfonyl Chloride2×HCID 103531188-Quinolinamine, 5-(trifluoromethyl)-2×

Product 1

HCID 60164194Pyridine-2-sulfonic acid (5-trifluoromethyl-quinolin-8-yl)-amideYield 31.7%

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) (125 mg, 0.58 mmol), pyridine-2-sulfonyl chloride (Intermediate 18) (125 mg, 0.70 mmol), pyridine (0.09 ml, 1.17 mmol), DMAP (cat.) and DCM (5 ml) gave the title compound (65 mg, 31%) after purification by column chromatography with n-hexane/DCM (50:50) as the eluent.

Sources & evidence

ORD record
ord-d0e2902fa3b040c2a9cfb93694e09d45
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Linked notes

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