Piperazin-2-one → 1-methyl-6-{4-[3-(3-oxo-piperazin-1-yl)-propyl]-3-trifluoromethyl-phenyl}-1H-imidazo[4,5-c]pyridine-4-carbonitrile

HRID 2079550Notes

Reaction equation

HRID 2079550 reaction equation
Br[CH2:2][CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:16]=[C:15]([C:17]#[N:18])[C:14]3[N:19]=[CH:20][N:21]([CH3:22])[C:13]=3[CH:12]=2)=[CH:7][C:6]=1[C:23]([F:26])([F:25])[F:24].[O:27]=[C:28]1[CH2:33][NH:32][CH2:31][CH2:30][NH:29]1>CN(C=O)C>[CH3:22][N:21]1[C:13]2[CH:12]=[C:11]([C:8]3[CH:9]=[CH:10][C:5]([CH2:4][CH2:3][CH2:2][N:32]4[CH2:31][CH2:30][NH:29][C:28](=[O:27])[CH2:33]4)=[C:6]([C:23]([F:26])([F:25])[F:24])[CH:7]=3)[N:16]=[C:15]([C:17]#[N:18])[C:14]=2[N:19]=[CH:20]1

Participants

4

Reactant 2

HCID 231360Piperazin-2-oneHCID 576575506-(4-(3-bromopropyl)-3-(trifluoromethyl)-phenyl)-1-methyl-1H-imidazo[4,5-c]pyridine-4-carbonitrile

Product 1

HCID 576575571-methyl-6-{4-[3-(3-oxo-piperazin-1-yl)-propyl]-3-trifluoromethyl-phenyl}-1H-imidazo[4,5-c]pyridine-4-carbonitrileYield 28.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6-(4-(3-Bromopropyl)-3-(trifluoromethyl)-phenyl)-1-methyl-1H-imidazo[4,5-c]pyridine-4-carbonitrile (50 mg) and 2-oxopiperazine (103 mg) in DMF (750 μl) were heated at 100° C. in a microwave for 25 minutes. Purification by basic phase preparative LCMS afforded 1-methyl-6-{4-[3-(3-oxo-piperazin-1-yl)-propyl]-3-trifluoromethyl-phenyl}-1H-imidazo[4,5-c]pyridine-4-carbonitrile (15 mg).

Workup

  1. customPurification by basic phase preparative LCMS

Sources & evidence

ORD record
ord-e3152451a5b8465ebf5becdaf01fb6b6
Source dataset
uspto-grants-2011_04
Patent number
US07932251B2

Reaction notes

Loading…