Deferiprone → HCID 86660355, compound

HRID 336106Notes

Reaction equation

HRID 336106 reaction equation
[OH:1][C:2]1[C:7](=[O:8])[CH:6]=[CH:5][N:4]([CH3:9])[C:3]=1[CH3:10].[C:11]1([CH3:21])[CH:16]=[CH:15][C:14]([S:17](Cl)(=[O:19])=[O:18])=[CH:13][CH:12]=1>N1C=CC=CC=1>[CH3:21][C:11]1[CH:16]=[CH:15][C:14]([S:17]([O:1][C:2]2[C:7](=[O:8])[CH:6]=[CH:5][N:4]([CH3:9])[C:3]=2[CH3:10])(=[O:19])=[O:18])=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 2972DeferiproneHCID 73974-Toluenesulfonyl chloride

Product 1

HCID 86660355HCID 86660355, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

3-Hydroxy-1,2-dimethylpyridin-4(1H)-one (0.2 g, 1.4 mmol) was reacted with p-toluenesulfonyl chloride (0.82 g, 4.3 mmol) in 10 mL of pyridine to afford PZBG-3b in 86% yield (0.35 g, 1.2 mmol). 1H NMR (500 MHz, CDCl3) δ=7.99 (d, J=8.4 Hz, 2H), 7.40 (d, J=7.6 Hz, 1H), 7.33 (d, J=8 Hz, 2H), 6.40 (d, J=7.2 Hz, 1H), 3.64 (s, 3H), 2.42 (s, 3H), 2.41 (s, 3H). 13C NMR (100 MHz, CDCl3) δ=170.71, 145.67, 145.54, 141.48, 134.07, 129.72, 128.96, 126.07, 117.53, 42.25, 22.00, 14.7. ESI-MS(+): m/z 294.05 [M+H]+, 315.97 [M+Na]+.

Workup

  1. customto afford PZBG-3b in 86% yield (0.35 g, 1.2 mmol)

Sources & evidence

ORD record
ord-726f1d40c06f41fba3553a65f0f6dd22
Source dataset
uspto-grants-2014_11
Patent number
US08889638B2

Reaction notes

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