ChemicalBook CAS DataBase List Dasatinib

Dasatinib synthesis

12synthesis methods

Product Name:Dasatinib
CAS Number:302962-49-8
Molecular formula:C22H26ClN7O2S
Molecular Weight:488.01

A concise and efficient route was developed for the synthesis of dasatinib. Reaction of 2-chlorothioa-zole (18) with n-butyllithium at low temperature followed by addition of 2-chloro-6-methylphenyl isocyanate (19) gave anilide 20 in 86% yield. The amide 20 was protected as corresponding 4-methoxy benzyl (PMB) anilide 22 in 95% yield which was subsequently reacted with 4- amino-6-chloro-2-methylpyrimidine (23) in the presence of sodium hydride in hot THF to give compound 24 in 83% yield. The PMB protecting group was then removed with triflic acid to give compound 25 in 99% yield. Compound 25 was reacted with 1-(2-hydroxyethyl)piperazine (26) in refluxing dioxane to give dasatinib (III) in 91% yield.

103-76-4
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302964-08-5 Synthesis

N-(2-Chloro-6-methylphenyl)-2-[(6-chloro-2-methyl-4-pyrimidinyl)amino]-5-thiazolecarboxamide

302964-08-5
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$7.00/250mg

302962-49-8
502 suppliers
$9.00/50mg

Yield:302962-49-8 97%

Reaction Conditions:

with tetrabutylammomium bromide in acetonitrile at 30 - 80;

Steps:

2 Preparation of Dasatinib Monohydrate

200 ml of acetonitrile was taken in RB flask and 10.0 g of 2-((6-chloro-2-methylpyrimidin-4-yl)amino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide (Formula I), 19.8 g of 1-(2-Hydroxyethyl)piperazine (Formula II), 12.85 g of triethyl amine and 10.0 g of TBAB were charged into it. The reaction mass was stirred for 10-15 mins at 30-35° C. and then heated to 80° C. and stirred for 20-22 h. The completion of reaction was checked with Thin Layer Chromatography (TLC) and 300 mL of water was slowly charged. The reaction mass was stirred for 45 mins at 80° C. and then cooled to 30-35° C. and further stirred for 1.5 hrs. The reaction mass was filtered, washed with 20 mL water and suck dried for 10-15 min at RT. The wet compound was unloaded and air dried for 30 mins at 30-35° C. The material was loaded to a vacuum tray drier at 30-35° C. and vacuum was applied. The material was dried at 30-35° C. for 1 h and slowly dryer temperature was raised to 50-55° C. where drying was carried out for 8-10 hrs. The solid product obtained was then cooled to 30-35° C. and vacuum was released to obtain 12.5 g of the title compound. [0073] Yield-97% HPLC Purity-99.42%

References:

US2015/57446,2015,A1 Location in patent:Page/Page column 0072; 0073

103-76-4
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1780-26-3 Synthesis

1780-26-3
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$10.00/10g

302964-24-5 Synthesis

2-Amino-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide

302964-24-5
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$9.00/250mg

302962-49-8
502 suppliers
$9.00/50mg

References

2-(4-(6-((5-((2-chloro-6-Methylphenyl)carbaMoyl)thiazol-2-yl)aMino)-2-MethylpyriMidin-4-yl)piperazin-1-yl)ethyl acetate

1245157-85-0
31 suppliers
$1200.00/100mg

302962-49-8
502 suppliers
$9.00/50mg

References

5-Thiazolecarboxamide, N-(2-chloro-6-methylphenyl)-2-[[2-methyl-6-[4-[2-(phenylmethoxy)ethyl]-1-piperazinyl]-4-pyrimidinyl]amino]-

1245157-70-3
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302962-49-8
502 suppliers
$9.00/50mg

References

5-Thiazolecarboxamide, N-(2-chloro-6-methylphenyl)-2-[[2-methyl-6-[4-[2-[(methylthio)methoxy]ethyl]-1-piperazinyl]-4-pyrimidinyl]amino]-

1245157-78-1
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302962-49-8
502 suppliers
$9.00/50mg

References

Dasatinib Related Search:

Nizatidine Epichlorohydrin 2-Amino-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide Imatinib Sunitinib Lapatinib Gefitinib 2-(METHYLSULFONYL)ETHANOL Dasatinib monohydrate