Deferiprone → HCID 86660356, compound

HRID 336107Notes

Reaction equation

HRID 336107 reaction equation
[OH:1][C:2]1[C:7](=[O:8])[CH:6]=[CH:5][N:4]([CH3:9])[C:3]=1[CH3:10].[N+:11]([C:14]1[CH:19]=[CH:18][C:17]([S:20](Cl)(=[O:22])=[O:21])=[CH:16][CH:15]=1)([O-:13])=[O:12]>N1C=CC=CC=1>[N+:11]([C:14]1[CH:15]=[CH:16][C:17]([S:20]([O:1][C:2]2[C:7](=[O:8])[CH:6]=[CH:5][N:4]([CH3:9])[C:3]=2[CH3:10])(=[O:22])=[O:21])=[CH:18][CH:19]=1)([O-:13])=[O:12]

Participants

4

Reactant 2

HCID 2972DeferiproneHCID 74044-Nitrobenzenesulfonyl chloride

Product 1

HCID 86660356HCID 86660356, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

3-Hydroxy-1,2-dimethylpyridin-4(1H)-one (0.2 g, 1.5 mmol) was reacted with 4-nitrobenzenesulfonyl chloride (0.488 g, 2.2 mmol) in 10 mL of pyridine to afford PZBG-3c in 50% yield (0.23 g, 0.7 mmol). 1H NMR (400 MHz, CDCl3) δ=8.41-8.34 (m, 4H), 7.26 (d, J=7.6 Hz, 1H), 6.33 (d, J=7.6 Hz, 1H), 3.67 (s, 3H), 2.53 (s, 3H). 13C NMR (100 MHz, CDCl3) 6=170.9, 150.9, 144.9, 143.2, 140.9, 140.1, 130.4, 124.0, 118.4, 41.9, 14.6. ESI-MS(+): m/z 325.11 [M+H]+, 346.96 [M+Na]+.

Workup

  1. customto afford PZBG-3c in 50% yield (0.23 g, 0.7 mmol)

Sources & evidence

ORD record
ord-74f3484010724d79b3ed3868259a4dbc
Source dataset
uspto-grants-2014_11
Patent number
US08889638B2

Reaction notes

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