4-Methyl-3-[[4-(3-pyridinyl)-2-pyrimidinyl]amino]benzoic acid Chemical Properties

Melting point:

>257oC (dec.)

Boiling point:

587.9±60.0 °C(Predicted)

Density 

1.336

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

solubility 

DMSO (Slightly), Methanol (Slightly, Heated)

pka

4.35±0.10(Predicted)

form 

Solid

color 

Pale Beige

Stability:

Hygroscopic

InChI

InChI=1S/C17H14N4O2/c1-11-4-5-12(16(22)23)9-15(11)21-17-19-8-6-14(20-17)13-3-2-7-18-10-13/h2-10H,1H3,(H,22,23)(H,19,20,21)

InChIKey

LDLZPHLSVKGFSC-UHFFFAOYSA-N

SMILES

C(O)(=O)C1=CC=C(C)C(NC2=NC=CC(C3=CC=CN=C3)=N2)=C1

CAS DataBase Reference

641569-94-0(CAS DataBase Reference)

Safety Information

HS Code 

2933599590

4-Methyl-3-[[4-(3-pyridinyl)-2-pyrimidinyl]amino]benzoic acid Usage And Synthesis

Uses

4-Methyl-3-[[4-(3-pyridinyl)-2-pyrimidinyl]amino]benzoic acid is used in the preparation of (pyridinyl)-N-[(triazolyl)phenyl]pyrimidinamine derivatives and (pyridinyl)-N-[oxadiazolyl)phenyl]pyrimidinamine derivatives, and can be used in the detection of their activity as antileukemia agents (neoplastic stem cell leukemia). 4-Methyl-3-[[4-(3-pyridinyl)-2-pyrimidinyl]amino]benzoic acid is also a Nilotinib (N465300) intermediate, which might be useful in treatment of chronic myelogenous leukemia.

Synthesis

3- [(Aminoiminomethyl)amino] -4-methyl-benzoic acid methyl ester mononitrate (10 g),3-(Dimethylamino)-1-(pyridine-3-yl)prop-2-en-1-one (7.3 g), sodium hydroxide (1.7 g) was added to 1-butanol (100 mL) in a round bottom flask under nitrogen atmosphere. The reaction mass was heated to reflux temperature and stirred for 12 hours. Then the reaction mass was cooled to 25-35°C, and iN sodium hydroxide solution (1.5 g in 37 mL of DM water) was added to it throughout 20 mm. The reaction mass was heated to reflux temperature (120-125°C) and then cooled to 25-35°C. Hydrochloric acid was added to the reaction mass at 25-35°C and stirred for an hour. The material formed was filtered, washed with DM water and then dried under vacuum at 50-55°C to provide 4-Methyl-3-[[4-(3-pyridinyl)-2-pyrimidinyl]amino]benzoic acid (8.7 g).

4-Methyl-3-[[4-(3-pyridinyl)-2-pyrimidinyl]amino]benzoic acid(641569-94-0)Related Product Information

• 4-Dimethylaminobenzoic acid
• Methyl acrylate
• 4-Aminobenzoic acid
• Glycine
• Methyl cellulose
• Bensulfuron methyl
• METSULFURON METHYL
• Methylparaben
• Benzoic acid, 4-[1-[(2,4-diamino-6-pteridinyl)methyl]-3-butyn-1-yl]-
• Methyl
• 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline
• 4-(pyridine-2-yl) pyrimidin-2-amine
• Nilotinib N-Oxide
• 3-Amino-5-bromobenzotrifluoride
• 3-Iodo-4-methyl-N-[3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl]benzamide
• 3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)benzamide
• Nilotinib impurity 3
• Nilotinib Impurity 28