4-Chloromethyl-N-[4-methyl-3-[[4-(pyridin-3-yl)pyrimidin-2-yl]amino]phenyl]benzamide

Product Name: 4-Chloromethyl-N-[4-methyl-3-[[4-(pyridin-3-yl)pyrimidin-2-yl]amino]phenyl]benzamide
CAS No.: 404844-11-7
Chemical Name: 4-Chloromethyl-N-[4-methyl-3-[[4-(pyridin-3-yl)pyrimidin-2-yl]amino]phenyl]benzamide
Synonyms: Imatinib Impurity 43;Imatinib impurities3;PDGFRα kinase inhibitor 2;Imatinib genotoxic impurity D9;4-Chloromethyl-N-[4-methyl-3-[[4-(pyridin-3-yl)pyrimidin-2-y...;N-[5[[4-(Chloromethyl)benzoyl]amino]-2-methylphenyl]4-(3-pyridyl)-2-pyrimidine;4-Chloromethyl-N-[4-methyl-3-[[4-(pyridin-3-yl)pyrimidin-2-yl]amino]phenyl]benzamide;N-[5-[[4-(Chloromethyl)benzoyl]amino]-2-methylphenyl]-4-(3-pyridyl)-2-pyrimidineamine;Benzamide, 4-(chloromethyl)-N-[4-methyl-3-[[4-(3-pyridinyl)-2-pyrimidinyl]amino]phenyl]-;IMatinib interMediate (N-[4-Methyl-3-(4-pyridin-3-yl-pyriMidin-2-ylaMino)-phenyl]-4-ChloroMethyl BenzaMide)
CBNumber: CB01176522
Molecular Formula: C24H20ClN5O
Formula Weight: 429.9
MOL File: 404844-11-7.mol

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4-Chloromethyl-N-[4-methyl-3-[[4-(pyridin-3-yl)pyrimidin-2-yl]amino]phenyl]benzamide Property

Melting point:: 300°C (dec)
Density: 1.329
storage temp.: Keep in dark place,Sealed in dry,Store in freezer, under -20°C
solubility: Chloroform (Slightly), DMSO (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
form: Solid
pka: 12.99±0.70(Predicted)
color: Pale Yellow to Light Beige
CAS DataBase Reference: 404844-11-7

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

TRC

Product number: M325943
Product name: N-[4-Methyl-3-(4-pyridin-3-yl-pyrimidin-2-ylamino)-phenyl]-4-chloromethylBenzamide
Packaging: 1mg
Price: $105
Updated: 2021/12/16

AK Scientific

Product number: Z1737
Product name: 4-Chloromethyl-N-[4-methyl-3-[[4-(pyridin-3-yl)pyrimidin-2-yl]amino]phenyl]benzamide
Packaging: 100mg
Price: $197
Updated: 2021/12/16

American Custom Chemicals Corporation

Product number: HCH0014284
Product name: N-[4-METHYL-3-(4-PYRIDIN-3-YL-PYRIMIDIN-2-YLAMINO)-PHENYL]-4-CHLOROMETHYL BENZAMIDE
Purity: 95.00%
Packaging: 5MG
Price: $786.5
Updated: 2021/12/16

American Custom Chemicals Corporation

Product number: HCH0014284
Product name: N-[4-METHYL-3-(4-PYRIDIN-3-YL-PYRIMIDIN-2-YLAMINO)-PHENYL]-4-CHLOROMETHYL BENZAMIDE
Purity: 95.00%
Packaging: 50MG
Price: $1963.5
Updated: 2021/12/16

Medical Isotopes, Inc.

Product number: 12188
Product name: N-[4-Methyl-3-(4-pyridin-3-yl-pyrimidin-2-ylamino)-phenyl]-4-chloromethylBenzamide
Packaging: 25mg
Price: $2200
Updated: 2021/12/16

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4-Chloromethyl-N-[4-methyl-3-[[4-(pyridin-3-yl)pyrimidin-2-yl]amino]phenyl]benzamide Chemical Properties,Usage,Production

Chemical Properties

Off-White Solid

Uses

Gleevec Impurity

Synthesis

876-08-4

152460-10-1

404844-11-7

1. 6-Methyl-N1-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine (10.0 g, 36.0 mmol) and triethylamine (10.0 ml, 72.2 mmol) were dissolved in tetrahydrofuran (100 mL). The solution was cooled to 0 °C with stirring and kept for 10 min. 2. A solution of 4-(chloromethyl)benzoyl chloride (7.8 g, 41.4 mmol) in tetrahydrofuran (50 mL) was added dropwise. After stirring at 0 °C for 4 h, water (500 mL) was added dropwise to the reaction mixture and a pale yellow precipitate appeared. 3. The precipitate was collected by filtration, washed with water (2 x 500 ml) and dried under reduced pressure to afford 4-(chloromethyl)-N-(4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)phenyl)benzamide (15.1 g, yield: 97.4%) as a light yellow solid. 4. The substance (4 g, 93 mmol) and tert-butyl piperazine carboxylate (8.8 g, 465 mmol) were dissolved in N-methyl-2-pyrrolidone (20 mL). The solution was reacted under microwave conditions at 120°C for 1 hr. 5. After cooling to room temperature, dichloromethane (50 mL) was added to the reaction mixture. The resulting mixture was extracted with 1M hydrochloric acid (20mL). The acidic aqueous phase was neutralized with sodium carbonate and then extracted with dichloromethane (2 x 50 mL). 6. The combined organic layers were dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The crude product was purified by column chromatography (pentane/ethyl acetate) to give 4 g of 4-(4-((4-methyl-3-((4-(4-(pyridin-3-yl)pyrimidin-2- yl)tert-butyl)amino)phenyl)carbamoyl)benzyl)piperazine-1-carboxylate (72% yield) as a yellow solid. 7. The substance (580 mg, 1 mmol) was dissolved in an ethyl acetate solution of hydrochloric acid (5 mL, 4 M). The reaction mixture was stirred at room temperature for 2 hours and then concentrated under reduced pressure to give N-(4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)phenyl)-4-(piperazin-1-ylmethyl)benzamide hydrochloride. 8. (5Z,8Z,11Z,14Z,17Z)-Eicos-5,8,11,14,17-pentaenoic acid (EPA, 0.27 g, 0.92 mmol) was substituted with HATU (0.47 g, 1.24 mmol), triethylamine (0.25 g, 2.49 mmol), and N-(4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2 -yl)amino)phenyl)-4-(piperazin-1-ylmethyl)benzamide hydrochloride (0.4 g, 0.83 mmol) were reacted in 15 mL of dichloromethane. The reaction mixture was stirred at room temperature for 16 hours. 9. The reaction mixture was diluted with dichloromethane (100 mL). The organic layer was washed with aqueous ammonium chloride (3 x 100 mL), brine (3 x 100 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue obtained was purified by silica gel chromatography (gradient elution, 2:1 pentane/ethyl acetate to 100% ethyl acetate) to give 0.4 g of 4-((4-((5Z,8Z,11Z,14Z,17Z)-eicos-5,8,11,14,17-pentenoyl)piperazin-1-yl)methyl)-N-(4-methyl-3-((4-(pyridin-3-yl)) pyrimidin-2-yl)amino)phenyl)benzamide (62% yield).

References

[1] ChemMedChem, 2017, vol. 12, # 7, p. 487 - 501
[2] Patent: WO2014/204856, 2014, A1. Location in patent: Paragraph 0310-0311
[3] Patent: WO2006/71130, 2006, A2. Location in patent: Page/Page column 25-27
[4] Tetrahedron Letters, 2012, vol. 53, # 49, p. 6657 - 6661
[5] Patent: US9095622, 2015, B2. Location in patent: Page/Page column 33

4-Chloromethyl-N-[4-methyl-3-[[4-(pyridin-3-yl)pyrimidin-2-yl]amino]phenyl]benzamide Preparation Products And Raw materials

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4-Chloromethyl-N-[4-methyl-3-[[4-(pyridin-3-yl)pyrimidin-2-yl]amino]phenyl]benzamide Suppliers

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View Lastest Price from 4-Chloromethyl-N-[4-methyl-3-[[4-(pyridin-3-yl)pyrimidin-2-yl]amino]phenyl]benzamide manufacturers

Career Henan Chemical Co

Product: 4-Chloromethyl-N-[4-methyl-3-[[4-(pyridin-3-yl)pyrimidin-2-yl]amino]phenyl]benzamide 404844-11-7
Price: US $2.00/KG
Min. Order: 1g
Purity: 98%MIN
Supply Ability: ASK
Release date: 2020-01-07

404844-11-7, 4-Chloromethyl-N-[4-methyl-3-[[4-(pyridin-3-yl)pyrimidin-2-yl]amino]phenyl]benzamideRelated Search:

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4-Chloromethyl-N-[4-methyl-3-[[4-(pyridin-3-yl)pyrimidin-2-yl]amino]phenyl]benzamide

IMatinib interMediate (N-[4-Methyl-3-(4-pyridin-3-yl-pyriMidin-2-ylaMino)-phenyl]-4-ChloroMethyl BenzaMide)

4-Chloromethyl-N-[4-methyl-3-[[4-(pyridin-3-yl)pyrimidin-2-yl]amino]phenyl]benzamide N-[5-[[4-(Chloromethyl)benzoyl]amino]-2-methylphenyl]-4-(3-pyridyl)-2-pyrimidineamine

Imatinib genotoxic impurity D9

Imatinib impurity 18/4-(Chloromethyl)-N-(4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)phenyl)benzamide

Imatinib Impurity 43

[2H9]-N-[4-Methyl-3-(4-pyridin-3-yl-pyrimidin-2-ylamino)-phenyl]-4-chloromethyl Benzamide(Imatinib genotoxic impurity)

Benzamide, 4-(chloromethyl)-N-[4-methyl-3-[[4-(3-pyridinyl)-2-pyrimidinyl]amino]phenyl]-

4-Chloromethyl-N-[4-methyl-3-[[4-(pyridin-3-yl)pyrimidin-2-y...

Imatinib impurities3

PDGFRα kinase inhibitor 2

404844-11-7

C24H20ClN5O

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