Product Name

  • Name

    Masitinib (AB1010)

  • EINECS
  • CAS No. 790299-79-5
  • Article Data3
  • CAS DataBase
  • Density 1.281 g/cm3
  • Solubility
  • Melting Point 90-95oC
  • Formula C28H30N6OS
  • Boiling Point
  • Molecular Weight 498.652
  • Flash Point
  • Transport Information
  • Appearance
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 790299-79-5 (Masitinib (AB1010))
  • Hazard Symbols
  • Synonyms Benzamide,4-[(4-methyl-1-piperazinyl)methyl]-N-[4-methyl-3-[[4-(3-pyridinyl)-2-thiazolyl]amino]phenyl]-;
  • PSA 101.63000
  • LogP 5.27860

Synthetic route

N1-[4-(pyridin-3-yl)-1,3-thiazol-2-yl]-6-methyl-1,3-phenylenediamine
660837-08-1

N1-[4-(pyridin-3-yl)-1,3-thiazol-2-yl]-6-methyl-1,3-phenylenediamine

4-((4-methylpiperazin-1-yl)methyl)-benzoic acid methyl ester
314268-40-1

4-((4-methylpiperazin-1-yl)methyl)-benzoic acid methyl ester

masitinib
790299-79-5

masitinib

Conditions
ConditionsYield
Stage #1: N1-[4-(pyridin-3-yl)-1,3-thiazol-2-yl]-6-methyl-1,3-phenylenediamine With trimethylaluminum In hexane; dichloromethane at 5 - 15℃; for 2h;
Stage #2: 4-((4-methylpiperazin-1-yl)methyl)-benzoic acid methyl ester In hexane; dichloromethane at 20℃; for 21.1667h; Heating / reflux;
Stage #3: With sodium hydroxide; water In hexane; dichloromethane at 20℃; for 3h; Product distribution / selectivity;		78%
Stage #1: N1-[4-(pyridin-3-yl)-1,3-thiazol-2-yl]-6-methyl-1,3-phenylenediamine With trimethylaluminum In dichloromethane; toluene at 0 - 20℃; for 0.5h;
Stage #2: 4-((4-methylpiperazin-1-yl)methyl)-benzoic acid methyl ester In dichloromethane; toluene for 5h; Heating / reflux;		72%
Stage #1: N1-[4-(pyridin-3-yl)-1,3-thiazol-2-yl]-6-methyl-1,3-phenylenediamine With trimethylaluminum In dichloromethane; toluene at 0 - 20℃; for 0.5h;
Stage #2: 4-((4-methylpiperazin-1-yl)methyl)-benzoic acid methyl ester In dichloromethane; toluene for 5h; Heating / reflux;		72%
N1-[4-(pyridin-3-yl)-1,3-thiazol-2-yl]-6-methyl-1,3-phenylenediamine
660837-08-1

N1-[4-(pyridin-3-yl)-1,3-thiazol-2-yl]-6-methyl-1,3-phenylenediamine

4-(4-Methylpiperazin-1-ylmethyl)benzoyl chloride
148077-69-4

4-(4-Methylpiperazin-1-ylmethyl)benzoyl chloride

masitinib
790299-79-5

masitinib

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 30℃; for 10h; Product distribution / selectivity;65%
N1-[4-(pyridin-3-yl)-1,3-thiazol-2-yl]-6-methyl-1,3-phenylenediamine
660837-08-1

N1-[4-(pyridin-3-yl)-1,3-thiazol-2-yl]-6-methyl-1,3-phenylenediamine

4-(4-methylpiperazin-1-ylmethyl)benzoic acid
106261-48-7

4-(4-methylpiperazin-1-ylmethyl)benzoic acid

masitinib
790299-79-5

masitinib

Conditions
ConditionsYield
With 2-chloro-1-methyl-pyridinium iodide In dichloromethane at 20℃; for 7h; Product distribution / selectivity;51%
1-methyl-piperazine
109-01-3

1-methyl-piperazine

methyl 4-formylbenzoate
1571-08-0

methyl 4-formylbenzoate

masitinib
790299-79-5

masitinib

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: trifluoroacetic acid / acetonitrile / 1 h / 20 °C
1.2: 20 °C
2.1: trimethylaluminum / dichloromethane; toluene / 0.5 h / 0 - 20 °C
2.2: 5 h / Heating / reflux
View Scheme
methyl-3-pyridylketone
350-03-8

methyl-3-pyridylketone

masitinib
790299-79-5

masitinib

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: hydrogen bromide; bromine / acetic acid / 2 h / 0 - 75 °C
2.1: potassium hydrogencarbonate / ethanol / 20 h / 75 °C
3.1: trifluoroacetic acid / dichloromethane / 2 h / 20 °C
4.1: trimethylaluminum / dichloromethane; toluene / 0.5 h / 0 - 20 °C
4.2: 5 h / Heating / reflux
View Scheme
2-[(2-methyl-5-tert-butoxycarbonylaminophenyl)amino]-4-(3-pyridyl)thiazole

2-[(2-methyl-5-tert-butoxycarbonylaminophenyl)amino]-4-(3-pyridyl)thiazole

masitinib
790299-79-5

masitinib

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: trifluoroacetic acid / dichloromethane / 2 h / 20 °C
2.1: trimethylaluminum / dichloromethane; toluene / 0.5 h / 0 - 20 °C
2.2: 5 h / Heating / reflux
View Scheme
N-(2-methyl-5-tert-butoxycarbonylamino)phenyl-thiourea
660838-06-2

N-(2-methyl-5-tert-butoxycarbonylamino)phenyl-thiourea

masitinib
790299-79-5

masitinib

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: potassium hydrogencarbonate / ethanol / 20 h / 75 °C
2.1: trifluoroacetic acid / dichloromethane / 2 h / 20 °C
3.1: trimethylaluminum / dichloromethane; toluene / 0.5 h / 0 - 20 °C
3.2: 5 h / Heating / reflux
View Scheme
2-methyl-5-tert-butoxycarbonylaminoaniline hydrobromide salt
790299-78-4

2-methyl-5-tert-butoxycarbonylaminoaniline hydrobromide salt

masitinib
790299-79-5

masitinib

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: benzoyl chloride / acetone / 1 h / Heating / reflux
2.1: potassium hydrogencarbonate / ethanol / 20 h / 75 °C
3.1: trifluoroacetic acid / dichloromethane / 2 h / 20 °C
4.1: trimethylaluminum / dichloromethane; toluene / 0.5 h / 0 - 20 °C
4.2: 5 h / Heating / reflux
View Scheme
3-(2-bromoacetyl)pyridine hydrobromide
17694-68-7

3-(2-bromoacetyl)pyridine hydrobromide

masitinib
790299-79-5

masitinib

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: potassium hydrogencarbonate / ethanol / 20 h / 75 °C
2.1: trifluoroacetic acid / dichloromethane / 2 h / 20 °C
3.1: trimethylaluminum / dichloromethane; toluene / 0.5 h / 0 - 20 °C
3.2: 5 h / Heating / reflux
View Scheme
masitinib
790299-79-5

masitinib

methanesulfonic acid
75-75-2

methanesulfonic acid

Masitinib mesylate
1048007-93-7

Masitinib mesylate

Conditions
ConditionsYield
In ethanol at 25 - 70℃; for 6h;85%
masitinib
790299-79-5

masitinib

methanesulfonic acid
75-75-2

methanesulfonic acid

masitinib mesilate

masitinib mesilate

Conditions
ConditionsYield
In methanol at 25℃; for 13h; Temperature;8.5 g

Masitinib Chemical Properties

IUPAC name: 4-[(4-Methylpiperazin-1-yl)methyl]-N-[4-methyl-3-[(4-pyridin-3-yl-1,3-thiazol-2-yl)amino]phenyl]benzamide
Following is the structure of Masitinib (CAS NO.790299-79-5):
 
Molecular Formula: C28H30N6OS
Molecular Weight: 498.64 g/mol
Index of Refraction: 1.682
Density: 1.281 g/cm3
Surface Tension of Masitinib (CAS NO.790299-79-5): 63.612 dyne/cm 
Canonical SMILES: CC1=C(C=C(C=C1)NC(=O)C2=CC=C(C=C2)CN3CCN(CC3)C)NC4=NC(=CS4)C5=CN=CC=C5
InChI: InChI=1S/C28H30N6OS/c1-20-5-10-24(16-25(20)31-28-32-26(19-36-28)23-4-3-11-29-17-23)30-27(35)22-8-6-21(7-9-22)18-34-14-12-33(2)13-15-34/h3-11,16-17,19H,12-15,18H2,1-2H3,(H,30,35)(H,31,32)
InChIKey: WJEOLQLKVOPQFV-UHFFFAOYSA-N

Masitinib Uses

 Masitinib (CAS NO.790299-79-5) is a protein kinase inhibitor and antineoplastic agent.

Masitinib Specification

 Masitinib , its cas register number is 790299-79-5. It also can be called  4-[(4-Methyl-1-piperazinyl)methyl]-N-[4-methyl-3-[[4-(3-pyridinyl)-2-thiazolyl]amino]phenyl]benzamide ; and AB 1010 .

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