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

CAS: 641569-94-0

Molecular Formula: C17H14N4O2

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Description

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

641569-94-0 – Names and Identifiers

Name	4-Methyl-3-[[4-(3-pyridinyl)-2-pyrimidinyl]amino]benzoic acid
Synonyms	Nilotinib Intemediate 2 Nilotinib EP Impurity D 4-Methyl-3-((4-(pyridin-3-yl) 4-Methyl-3-[[4-(3-pyridinyl)-2-pyrimidiny]amino]benzoicacid 4-methyl-3-(4-(pyridin-3-yl)pyrimidin-2-ylamino)benzoic acid Benzoic acid, 4-methyl-3-[[4-(3-pyridinyl)-2-pyrimidinyl]amino]- 2-[(5-Carboxy-2-methylphenyl)amino]-4-(pyridin-3-yl)pyrimidine, 3-{2-[(5-Carboxy-2-methylphenyl)amino]pyrimidin-4-yl}pyridine
CAS	641569-94-0
EINECS	629-968-8
InChI	InChI=1/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)

641569-94-0 – Physico-chemical Properties

Molecular Formula	C17H14N4O2
Molar Mass	306.32
Density	1.336
Melting Point	>257oC (dec.)
Boling Point	587.9±60.0 °C(Predicted)
Flash Point	309.367°C
Solubility	DMSO (Slightly), Methanol (Slightly, Heated)
Vapor Presure	0mmHg at 25°C
Appearance	Solid
Color	Pale Beige
pKa	4.35±0.10(Predicted)
Storage Condition	under inert gas (nitrogen or Argon) at 2–8 °C
Stability	Hygroscopic
Refractive Index	1.676
Physical and Chemical Properties	4-methyl -3-[[4-(3-pyridyl)-2-pyrimidinyl] amino] Benzoic acid is a yellow-white solid with some solubility in methanol and dimethyl sulfoxide.

641569-94-0 – Reference Information

Use

4-methyl -3-[[4-(3-pyridyl)]-2-pyrimidinyl] amino] benzoic acid plays an important role in the synthesis of the antitumor drug molecule nilotinib, however, the carboxyl group in its structure can still be converted into acid chloride and then into ester group by the action of dichlorosulfoxide.

synthetic method

LiOH (0.24g, 10 mmol, 8 eq.) dissolve in a 3:1 mixture of methanol and water (12 ml)
add 4-methyl -3-[[4-(3-pyridyl)] to the above reaction mixture-2-pyrimidinyl] amino] benzoic acid methyl ester (0.4g,1.25
mmol), the reaction mixture was stirred at room temperature for 8 hours, the reaction was acidified to pH =
1 with 1 N HCl, the solvent was concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography, the target product 4-methyl -3-[[4-(3-pyridyl)-2-pyrimidinyl] amino] benzoic acid was obtained.

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