Pyridine → HCID 68183235, compound

HRID 513489Notes

Reaction equation

HRID 513489 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2.[F:12][C:13]([F:25])([F:24])[C:14]1[CH:15]=[C:16]([S:20](Cl)(=[O:22])=[O:21])[CH:17]=[N:18][CH:19]=1.N1C=CC=CC=1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[N:10]1[C:11]2[C:6](=[CH:5][CH:4]=[CH:3][C:2]=2[NH:1][S:20]([C:16]2[CH:17]=[N:18][CH:19]=[C:14]([C:13]([F:25])([F:12])[F:24])[CH:15]=2)(=[O:22])=[O:21])[CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 113598-AminoquinolineHCID 552793645-TRIFLUOROMETHYL-PYRIDINE-3-SULFONYL CHLORIDE2×

Product 1

HCID 68183235HCID 68183235, compoundYield 17.7%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

In a similar fashion using route 14 general procedure 27, 8-aminoquinoline (70 mg, 0.48 mmol), 5-trifluoromethyl-pyridine-3-sulfonyl chloride (Intermediate 442) (153 mg, 0.63 mmol), DMAP (cat.), pyridine (1.5 ml) and DCM (2 ml) gave the title compound (30 mg, 11%) after purification by column chromatography with n-hexane/EtOAc (85:15) as the eluent.

Sources & evidence

ORD record
ord-31f169e4bc9d45299c0b9a0217f75be3
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

Loading…