N-(2-chloroethyl)-2-methyl-3-hydroxy-4-pyridinone → N-(4-propargylpiperazin-1-ylethyl)-2-methyl-3-hydroxy-4-pyridinone

HRID 2358948Notes

Reaction equation

HRID 2358948 reaction equation
Cl[CH2:2][CH2:3][N:4]1[CH:9]=[CH:8][C:7](=[O:10])[C:6]([OH:11])=[C:5]1[CH3:12].[CH2:13]([N:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1)[C:14]#[CH:15]>>[CH2:13]([N:16]1[CH2:21][CH2:20][N:19]([CH2:2][CH2:3][N:4]2[CH:9]=[CH:8][C:7](=[O:10])[C:6]([OH:11])=[C:5]2[CH3:12])[CH2:18][CH2:17]1)[C:14]#[CH:15]

Participants

3

Reactant 2

HCID 337279N-(2-chloroethyl)-2-methyl-3-hydroxy-4-pyridinoneHCID 146273691-(2-Propynyl)piperazine

Product 1

HCID 58730241N-(4-propargylpiperazin-1-ylethyl)-2-methyl-3-hydroxy-4-pyridinone

Procedure

The title compound was prepared as described in Scheme D by reaction of N-(2-chloroethyl)-2-methyl-3-hydroxy-4-pyridinone (H2, Appendix VII) (prepared as described in Bijaya L. Rai, Lotfollah Dekhordi, Hicham Khodr, Yi Jin, Zudong Liu, and Robert C. Hider J. Med. Chem. 1998, 41, 3347-3359) with N-propargylpiperazine (obtained as in step (iii) in Example 2):

Sources & evidence

ORD record
ord-0024b08342d24913adc15df55e6a0a2e
Source dataset
uspto-grants-2014_04
Patent number
US08685955B2

Reaction notes

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