Pyridine → HCID 68183163, compound

HRID 513531Notes

Reaction equation

HRID 513531 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:14]2[C:9](=[C:10]([NH2:15])[CH:11]=[CH:12][CH:13]=2)[N:8]=[CH:7][CH:6]=1)=[O:4].[N+:16]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[S:25](Cl)(=[O:27])=[O:26])([O-:18])=[O:17].N1C=CC=CC=1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH3:1][O:2][C:3]([C:5]1[C:14]2[C:9](=[C:10]([NH:15][S:25]([C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=3[N+:16]([O-:18])=[O:17])(=[O:26])=[O:27])[CH:11]=[CH:12][CH:13]=2)[N:8]=[CH:7][CH:6]=1)=[O:4]

Participants

6

Reactant 3

HCID 1049PyridineHCID 155402-Nitrobenzenesulfonyl chlorideHCID 68183301HCID 68183301, compound2×

Product 1

HCID 68183163HCID 68183163, compoundYield 93.5%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

In a similar fashion using route 14 general procedure 27, 8-amino-quinoline-4-carboxylic acid methyl ester (Intermediate 475) (370 mg, 1.38 mmol), 2-nitrobenzenesulfonyl chloride (530 mg, 2.3 mmol), DMAP (cat.), pyridine (0.44 ml, 5.4 mmol) and DCM (15 ml) gave the title compound (500 mg, 70%) after purification by column chromatography with DCM/MeOH (99:1) as the eluent.

Sources & evidence

ORD record
ord-564da42ccbaa48e2b7b00e6ba0369157
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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