Pyridine → HCID 68183181, compound

HRID 513521Notes

Reaction equation

HRID 513521 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([S:9](Cl)(=[O:11])=[O:10])=[C:5]([N+:13]([O-:15])=[O:14])[CH:4]=1)#[N:2].[N:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([S:9]([NH:2][C:1]2[CH:3]=[CH:4][CH:5]=[C:20]3[C:21]=2[N:16]=[CH:17][CH:18]=[CH:19]3)(=[O:11])=[O:10])=[C:5]([N+:13]([O-:15])=[O:14])[CH:4]=1)#[N:2]

Participants

5

Reactant 2

HCID 1049PyridineHCID 5459493798279-07-32×

Product 1

HCID 68183181HCID 68183181, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

In a similar fashion using route 14 general procedure 27, 8-aminoqunoline (0.60 g, 4.16 mmol), 4-cyano-2-nitro-benzenesulfonyl chloride (Intermediate 217) (1.33 g, 5.41 mmol), DMAP (cat), pyridine (5 ml) and DCM (3 ml) gave the title compound (0.65 g, 46%) after purification by column chromatography with n-hexane/EtOAc (90:10) as the eluent.

Sources & evidence

ORD record
ord-ee5c7b1f3a4f481f93026b0ab8d3dfd2
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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