Pyridine → HCID 68183322, compound

HRID 513535Notes

Reaction equation

HRID 513535 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.[CH3:12][O:13][C:14]1[CH:15]=[CH:16][C:17]([N+:24]([O-:26])=[O:25])=[C:18]([S:20](Cl)(=[O:22])=[O:21])[CH:19]=1.N1C=CC=CC=1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH3:12][O:13][C:14]1[CH:15]=[CH:16][C:17]([N+:24]([O-:26])=[O:25])=[C:18]([S:20]([NH:1][C:2]2[CH:3]=[CH:4][CH:5]=[C:6]3[C:11]=2[N:10]=[CH:9][CH:8]=[CH:7]3)(=[O:21])=[O:22])[CH:19]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 113598-AminoquinolineHCID 79018155HCID 79018155, compound2×

Product 1

HCID 68183322HCID 68183322, compoundYield 30%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

In a similar fashion using route 14 general procedure 27, 8-aminoquinoline (950 mg, 6.59 mmol), 5-methoxy-2-nitro-benzenesulfonyl chloride (Intermediate 447) (2.15 g, 8.57 mmol), pyridine (4 ml), DMAP (cat.) and DCM (8 ml) gave the title compound (690 mg, 30%) after purification by column chromatography with n-hexane/EtOAc (80:20) as the eluent.

Sources & evidence

ORD record
ord-05f2ad6dc0ab4829902b40eaea06b372
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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