BVD523

Base Information

• Chemical Name: BVD523
• CAS No.: 1956366-10-1
• Molecular Formula: C₂₁H₂₂Cl₂N₄O₂*ClH
• Molecular Weight: 469.798
• Hs Code.: 2933998090
• Mol file: 1956366-10-1.mol

Synonyms:

Chemical Property of BVD523

Chemical Property:

• Melting Point: 231-232°C
• Storage Temp.: -20°C Freezer
• Solubility.: DMSO (Slightly), Methanol (Slightly)

Purity/Quality:

99%, ^*data from raw suppliers

Ulixertinib Hydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Description: Ulixertinib is a reversible ERK1/2 inhibitor that demonstrates an IC50 value of <0.3 nM for ERK2. In A375 melanoma cells with b-RafV600E mutation, it has been reported to reduce the levels of phosphorylated ERK2 and the downstream kinase RSK (IC50s = 4.1 and 0.14 μM, respectively). Ulixertinib has also been shown to inhibit A375 cell proliferation with an IC50 value of 180 nM.
• Uses: Ulixertinib Hydrochloride is an acid salt of Ulixertinib (U700830), a potent and reversible ERK1/ERK2 inhibitor with IC50 of <0.3 nM for ERK2. Inhibits cell proliferation. Anti-cancer.

Technology Process of BVD523

There total 5 articles about BVD523 which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

5-chloro-4-iodo-N-isopropylpyridin-2-amine (869886-87-3) → 4-(5-chloro-2-isopropylaminopyridin-4-yl)-1H-pyrrole-2-carboxylicacid[1-(3-chlorophenyl)-2-hydroxyethyl]amide hydrochloride (1956366-10-1)

Guidance literature:

Multi-step reaction with 4 steps

1: sodium carbonate; palladium diacetate; tricyclohexylphosphine tetrafluoroborate / 1,2-dimethoxyethane; water / 4 h / 20 - 85 °C / 760.05 Torr / Inert atmosphere; Large scale

2: diethylamine; water; lithium hydroxide monohydrate / tetrahydrofuran / 30 h / 15 - 70 °C / 760.05 Torr / Inert atmosphere; Large scale

3: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / -30 - 25 °C / Inert atmosphere; Large scale

4: hydrogenchloride / ethanol; methanol; isopropyl alcohol / 2 h / 70 - 75 °C / Large scale

With hydrogenchloride; lithium hydroxide monohydrate; water; palladium diacetate; sodium carbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; diethylamine; N-ethyl-N,N-diisopropylamine; tricyclohexylphosphine tetrafluoroborate; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; ethanol; water; N,N-dimethyl-formamide; isopropyl alcohol;

Reference yield:

4-(5-chloro-2-isopropylaminopyridin-4-yl)-1-(toluene-4-sulfonyl)-1H-pyrrole-2-carboxylic acid methyl ester (869886-88-4) → 4-(5-chloro-2-isopropylaminopyridin-4-yl)-1H-pyrrole-2-carboxylicacid[1-(3-chlorophenyl)-2-hydroxyethyl]amide hydrochloride (1956366-10-1)

Guidance literature:

Multi-step reaction with 3 steps

1: diethylamine; water; lithium hydroxide monohydrate / tetrahydrofuran / 30 h / 15 - 70 °C / 760.05 Torr / Inert atmosphere; Large scale

2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / -30 - 25 °C / Inert atmosphere; Large scale

3: hydrogenchloride / ethanol; methanol; isopropyl alcohol / 2 h / 70 - 75 °C / Large scale

With hydrogenchloride; lithium hydroxide monohydrate; water; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; diethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; ethanol; N,N-dimethyl-formamide; isopropyl alcohol;

Reference yield:

4-(5-chloro-2-isopropylaminopyridin-4-yl)-1-(toluene-4-sulfonyl)-1H-pyrrole-2-carboxylic acid methyl ester (869886-88-4) → 4-(5-chloro-2-isopropylaminopyridin-4-yl)-1H-pyrrole-2-carboxylic acid [1-(3-chlorophenyl)-2-hydroxyethyl]amide hydrochloride (1956366-10-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: lithium hydroxide monohydrate; diethylamine / water; tetrahydrofuran / 30 h / 15 - 70 °C / Inert atmosphere; Reflux; Large scale

2.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / -20 - 25 °C / Inert atmosphere; Large scale

2.2: -30 - 25 °C / Large scale

3.1: hydrogenchloride / ethanol; methanol; isopropyl alcohol / 2 h / 70 - 75 °C

With hydrogenchloride; lithium hydroxide monohydrate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; diethylamine; In tetrahydrofuran; methanol; ethanol; water; N,N-dimethyl-formamide; isopropyl alcohol;

upstream raw materials:

5-chloro-4-iodo-N-isopropylpyridin-2-amine

4-(5-chloro-2-isopropylaminopyridin-4-yl)-1-(toluene-4-sulfonyl)-1H-pyrrole-2-carboxylic acid methyl ester

4-(5-chloro-2-isopropylaminopyridin-4-yl)-1H pyrrole-2-carboxylic acid

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