Pyridine → HCID 35532075, compound

HRID 513520Notes

Reaction equation

HRID 513520 reaction equation
[CH3:1][O:2][C:3](=[O:17])[C:4]1[CH:9]=[CH:8][C:7]([S:10](Cl)(=[O:12])=[O:11])=[C:6]([N+:14]([O-:16])=[O:15])[CH:5]=1.[N:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH3:1][O:2][C:3](=[O:17])[C:4]1[CH:9]=[CH:8][C:7]([S:10](=[O:12])(=[O:11])[NH:14][C:6]2[CH:5]=[CH:4][CH:3]=[C:22]3[C:23]=2[N:18]=[CH:19][CH:20]=[CH:21]3)=[C:6]([N+:14]([O-:16])=[O:15])[CH:5]=1

Participants

5

Reactant 2

HCID 1049PyridineHCID 11208244methyl 4-(chlorosulfonyl)-3-nitrobenzoate2×

Product 1

HCID 35532075HCID 35532075, compoundYield 40%

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-chlorosulfonyl-3-nitro-benzoic acid methyl ester (Intermediate 438) (1.5 g, 5.41 mmol), DMAP (cat), pyridine (6 ml) and DCM (3 ml) gave the title compound (0.65 g, 40%) after purification by column chromatography with n-hexane/EtOAc (80:20) as the eluent.

Sources & evidence

ORD record
ord-47545e17e76d4ef5a06fadb90f708cbc
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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