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

HRID 513495Notes

Reaction equation

HRID 513495 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.[N:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[S:23](Cl)(=[O:25])=[O:24].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:23]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][N:17]=3)(=[O:25])=[O:24])[CH:13]=1)[N:10]=[CH:9][CH:8]=[CH:7]2

Participants

6

Reactant 3

HCID 1049PyridineHCID 3787675Pyridine-2-sulfonyl Chloride2×HCID 681830016-(Trifluoromethoxy)quinolin-8-amine2×

Product 1

HCID 60164195Pyridine-2-sulfonic acid (6-trifluoromethoxy-quinolin-8-yl)-amideYield 56.4%

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) (110 mg, 0.48 mmol), pyridine-2-sulfonyl chloride (Intermediate 18) (102 mg, 0.57 mmol), pyridine (0.08 ml, 0.96 mmol), DMAP (cat.) and DCM (5 ml) gave the title compound (100 mg, 56%) after purification by column chromatography with n-hexane/DCM (50:50) as the eluent.

Sources & evidence

ORD record
ord-51a94c31d0bd4ee991514fccd4792837
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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