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

HRID 513498Notes

Reaction equation

HRID 513498 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.[C:17]([C:19]1[N:24]=[CH:23][C:22]([S:25](Cl)(=[O:27])=[O:26])=[CH:21][CH:20]=1)#[N:18].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:17]#[N:18])=[CH:20][CH:21]=3)(=[O:26])=[O:27])[CH:13]=1)[N:10]=[CH:9][CH:8]=[CH:7]2

Participants

6

Reactant 3

HCID 1049PyridineHCID 470031906-Cyanopyridine-3-sulfonyl chloride2×HCID 681830016-(Trifluoromethoxy)quinolin-8-amine2×

Product 1

HCID 601643056-Cyano-pyridine-3-sulfonic acid (6-trifluoromethoxy-quinolin-8-yl)-amideYield 35.2%

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) (125 mg, 0.54 mmol), 6-cyano-pyridine-3-sulfonyl chloride (Intermediate 19) (132 mg, 0.65 mmol), pyridine (0.09 ml, 1.09 mmol), DMAP (cat.) and DCM (10 ml) gave the title compound (75 mg, 35%) after purification by column chromatography with n-hexane/DCM (50:50) as the eluent.

Sources & evidence

ORD record
ord-7453ca1b61634487825b91a15b7ff0cb
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

Loading…