3-PYRIDINECARBOXAMIDE, 4-(2-METHYLPHENYL)-6-(4-METHYL-1-PIPERAZINYL)- Chemical Properties

Melting point:

164-165℃

Boiling point:

498.1±45.0 °C(Predicted)

Density 

1.165

storage temp. 

2-8°C

pka

15.82±0.50(Predicted)

Appearance

White to off-white Solid

InChI

InChI=1S/C18H22N4O/c1-13-5-3-4-6-14(13)15-11-17(20-12-16(15)18(19)23)22-9-7-21(2)8-10-22/h3-6,11-12H,7-10H2,1-2H3,(H2,19,23)

InChIKey

UQTDFKWGXOVHFZ-UHFFFAOYSA-N

SMILES

C1=NC(N2CCN(C)CC2)=CC(C2=CC=CC=C2C)=C1C(N)=O

CAS DataBase Reference

342417-01-0

3-PYRIDINECARBOXAMIDE, 4-(2-METHYLPHENYL)-6-(4-METHYL-1-PIPERAZINYL)- Usage And Synthesis

Application

Netupitant is a selective antagonist of the human substance P/neurokine 1 (NK1) receptor. Panostron is a 5-HT3 receptor antagonist with a strong binding affinity for this receptor and low or no affinity for other receptors. 6-(4-methylpiperazin-1-yl)-4-(2-methylphenyl)nicotinamide is an organic synthesis intermediate and pharmaceutical intermediate used in laboratory research and development processes and chemical and pharmaceutical synthesis, primarily as an intermediate for netupitant.

Synthesis

Step 3: 1.0 g (4.05 mmol) of 6-chloro-4-o-tolylnicotinamide was dissolved in 9.0 mL of N-methylpiperazine, heated to 100 °C and the reaction was maintained for 2 hours. Upon completion of the reaction, the excess N-methylpiperazine was removed by high vacuum distillation. The residue was purified by silica gel column chromatography using dichloromethane as eluent to give 1.2 g (95% yield) of the target compound, 6-(4-methylpiperazin-1-yl)-4-(o-tolyl)nicotinamide, the product was a pale yellow crystalline foam. Mass spectrometry (ISP): m/z 311 ([M+H]+, 100%), 254 (62%).

References

[1] Patent: US8426450, 2013, B1. Location in patent: Page/Page column 25
[2] Patent: US9403772, 2016, B2. Location in patent: Page/Page column 30
[3] Journal of Organic Chemistry, 2006, vol. 71, # 5, p. 2000 - 2008
[4] Patent: JP2015/17121, 2015, A. Location in patent: Paragraph 0153

3-PYRIDINECARBOXAMIDE, 4-(2-METHYLPHENYL)-6-(4-METHYL-1-PIPERAZINYL)-(342417-01-0)Related Product Information

• 2-[3,5-bis(trifluoromethyl)phenyl]-N,2-dimethyl-N-[4-(2-methylphenyl)-6-(4-methylpiperazin-1-yl)pyridin-3-yl]propanamide
• Methyl (6-(4-Methylpiperazin-1-yl)-4-(o-tolyl)pyridin-3-yl)carbaMate
• 3-PYRIDINAMINE, N-METHYL-4-(2-METHYLPHENYL)-6-(4-METHYL-1-PIPERAZINYL)-
• N-tert-butyl-6-chloro-4-(o-tolyl)nicotinamide
• 3-PYRIDINECARBOXAMIDE, 4-(2-METHYLPHENYL)-6-(4-METHYL-1-PIPERAZINYL)-
• 6-(DIMETHYLAMINO)-4-METHYLNICOTINALDEHYDE
• 3-PYRIDINECARBOXAMIDE, N-(1,1-DIMETHYLETHYL)-4-(2-METHYLPHENYL)-6-(4-METHYL-1-PIPERAZINYL)-
• N-METHYL-6-(4-METHYL-PIPERAZIN-1-YL)-4-O-TOLYL-NICOTINAMIDE