6-Aminonicotinic acid → (6-Aminopyridin-3-yl)(4-methylpiperazin-1-yl)methanone

HRID 2109020Notes

Reaction equation

HRID 2109020 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][N:3]=1.C1N=CN(C(N2C=NC=C2)=O)C=1.[CH3:23][N:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1>CN(C)C=O>[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([N:27]2[CH2:28][CH2:29][N:24]([CH3:23])[CH2:25][CH2:26]2)=[O:8])=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 184966-Aminonicotinic acidHCID 531671-MethylpiperazineHCID 682631,1'-Carbonyldiimidazole

Product 1

HCID 57781845(6-Aminopyridin-3-yl)(4-methylpiperazin-1-yl)methanone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

3.00 g 6-amino-nicotinic acid are dissolved in 30 ml of dimethylformamide and 4.05 g of N,N-carbonyldiimidazole are added. The mixture is briefly heated to 70° C. and then stirred for a further hour at ambient temperature. After this time 4.85 ml of N-methylpiperazine are added and the mixture is stirred for 12 hours at ambient temperature. The solvent is eliminated and the residue is purified through a silica gel column with methylene chloride/ethanol/ammonia 7:1:0.1 as eluant.

Workup

  1. stirringthe mixture is stirred for 12 hours at ambient temperature
  2. customthe residue is purified through a silica gel column with methylene chloride/ethanol/ammonia 7:1:0.1 as eluant

Sources & evidence

ORD record
ord-aee4b24eeb624d02838609c3786e4880
Source dataset
uspto-grants-2009_04
Patent number
US07514468B2

Reaction notes

Loading…