Pyridine → HCID 68183048, compound

HRID 513528Notes

Reaction equation

HRID 513528 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:9]([NH2:12])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.[F:13][C:14]1[C:19]([F:20])=[CH:18][C:17]([S:21](Cl)(=[O:23])=[O:22])=[C:16]([N+:25]([O-:27])=[O:26])[CH:15]=1.N1C=CC=CC=1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[Cl:1][C:2]1[CH:11]=[CH:10][C:9]([NH:12][S:21]([C:17]2[CH:18]=[C:19]([F:20])[C:14]([F:13])=[CH:15][C:16]=2[N+:25]([O-:27])=[O:26])(=[O:22])=[O:23])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2

Participants

6

Reactant 3

HCID 1049PyridineHCID 2248605-Chloroquinolin-8-amine2×HCID 866697531394083-84-12×

Product 1

HCID 68183048HCID 68183048, compoundYield 14.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

In the similar fashion using route 14 general procedure 27, 5-chloro-quinolin-8-ylamine (Intermediate 27) (400 mg, 2.2 mmol), 4,5-difluoro-2-nitro-benzenesulfonyl chloride (Intermediate 219) (750 mg, 2.9 mmol), DMAP (cat.) and pyridine (5 ml) and DCM (5 ml) gave the title compound (125 mg, 14%) after purification by column chromatography with DCM as the eluent.

Sources & evidence

ORD record
ord-aaba0b0e1ba4408fa75056bd916581ad
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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