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Masitinib
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Name

Masitinib

 EINECS N/A
CAS No. 790299-79-5 Density 1.281 g/cm3
PSA 101.63000 LogP 5.27860
Solubility N/A Melting Point 90-95oC
Formula C28H30N6OS Boiling Point N/A
Molecular Weight 498.652 Flash Point N/A
Transport Information N/A Appearance N/A
Safety Risk Codes N/A
Molecular Structure Molecular Structure of 790299-79-5 (Masitinib (AB1010)) Hazard Symbols N/A
Synonyms

Benzamide,4-[(4-methyl-1-piperazinyl)methyl]-N-[4-methyl-3-[[4-(3-pyridinyl)-2-thiazolyl]amino]phenyl]-;

Article Data 3

Masitinib Synthetic route

660837-08-1

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

314268-40-1

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

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%
660837-08-1

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

148077-69-4

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

790299-79-5

masitinib

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 30℃; for 10h; Product distribution / selectivity;65%
660837-08-1

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

106261-48-7

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

790299-79-5

masitinib

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

1-methyl-piperazine

1571-08-0

methyl 4-formylbenzoate

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
350-03-8

methyl-3-pyridylketone

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

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
660838-06-2

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

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
790299-78-4

2-methyl-5-tert-butoxycarbonylaminoaniline hydrobromide salt

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
17694-68-7

3-(2-bromoacetyl)pyridine hydrobromide

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
790299-79-5

masitinib

75-75-2

methanesulfonic acid

1048007-93-7

Masitinib mesylate

Conditions
ConditionsYield
In ethanol at 25 - 70℃; for 6h;85%

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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