ChemicalBook CAS DataBase List Masitinib

Masitinib synthesis

7synthesis methods

Product Name:Masitinib
CAS Number:790299-79-5
Molecular formula:C28H30N6OS
Molecular Weight:498.64

4-Methyl-n3-(4-pyridin-3-yl-thiazol-2-yl)-benzene-1,3-diaMine

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METHYL 4-[(4-METHYLPIPERAZIN-1-YL)METHYL]BENZOATE

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790299-79-5
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Yield:790299-79-5 78%

Reaction Conditions:

Stage #1: N₁-[4-(pyridin-3-yl)-1,3-thiazol-2-yl]-6-methyl-1,3-phenylenediaminewith trimethylaluminum in hexane;dichloromethane at 5 - 15; for 2 h;
Stage #2: 4-((4-methylpiperazin-1-yl)methyl)-benzoic acid methyl ester in hexane;dichloromethane at 20; for 21.1667 h;Heating / reflux;
Stage #3: with sodium hydroxide;water in hexane;dichloromethane at 20; for 3 h;Product distribution / selectivity;

Steps:

4.A

Method A In a reactor and under low nitrogen pressure, add 4-Methyl-N3-(4-pyridin-3-yl-thiazol- 2-yl)-benzene-l,3-diamine (95 g, 336.45 mmol), dichloromethane (2 L). To this suspension cooled to temperature of 5°C was added dropwise 2M/n-hexane solution of trimethylaluminium (588 mL). The reaction mixture was brought progressively to 15°C, and maintained for 2 h under stirring. 4-(4-Methyl-piperazin-l-ylmethyl)-benzoic acid methyl ester (100 g, 402.71 mmol) in dichloromethane (200 mL) was added for 10 minutes. After 1 h stirring at room temperature, the reaction mixture was heated to reflux for 20 h and cooled to room temperature. This solution was transferred dropwise via a cannula to a reactor containing 2N NaOH (2.1 L) cooled to 5°C. After stirring for 3 h at room temperature, the precipitate was filtered through Celite. The solution was extracted with dichloromethane and the organic layer was washed with water and saturated sodium chloride solution, dried over MgSO₄ and concentrated under vacuum. The brown solid obtained was recrystallized from /-Pr₂O to give 130.7 g (78%) of a beige powder.

References:

WO2008/98949,2008,A2 Location in patent:Page/Page column 20-21

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