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HomeProduct name list4-Methyl-3-[[4-(3-pyridinyl)-2-pyrimidinyl]amino]benzoic acid

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

  • CAS NO.:641569-94-0
  • Empirical Formula: C17H14N4O2
  • Molecular Weight: 306.32
  • MDL number: MFCD11521324
  • EINECS: 629-968-8
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-04-28 19:50:54
4-Methyl-3-[[4-(3-pyridinyl)-2-pyrimidinyl]amino]benzoic acid Structural

What is 4-Methyl-3-[[4-(3-pyridinyl)-2-pyrimidinyl]amino]benzoic acid?

The Uses of 4-Methyl-3-[[4-(3-pyridinyl)-2-pyrimidinyl]amino]benzoic acid

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).

Physical properties

4-Methyl-3-[[4-(3-pyridinyl)-2-pyrimidinyl]amino]benzoic acid is a pale beige solid, soluble in DMSO (Slightly), Methanol (Slightly, Heated).

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

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)
form  Solid
pka 4.35±0.10(Predicted)
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)
CAS DataBase Reference 641569-94-0(CAS DataBase Reference)

Safety information for 4-Methyl-3-[[4-(3-pyridinyl)-2-pyrimidinyl]amino]benzoic acid

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H315:Skin corrosion/irritation
H319:Serious eye damage/eye irritation
H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes P261:Avoid breathing dust/fume/gas/mist/vapours/spray.
P271:Use only outdoors or in a well-ventilated area.
P280:Wear protective gloves/protective clothing/eye protection/face protection.

Computed Descriptors for 4-Methyl-3-[[4-(3-pyridinyl)-2-pyrimidinyl]amino]benzoic acid

InChIKey LDLZPHLSVKGFSC-UHFFFAOYSA-N
SMILES C(O)(=O)C1=CC=C(C)C(NC2=NC=CC(C3=CC=CN=C3)=N2)=C1

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