VRT752271
- Product Name
- VRT752271
- CAS No.
- 869886-67-9
- Chemical Name
- VRT752271
- Synonyms
- CS-725;VRT752271;BVD-523FB;Padsevonil;Ulixertinib;VRT752271 HCl;BVD-523 ( VRT752271);Ulixertinib (BVD-523);Ulixertinib, VRT752271;VRT-752271(Ulixertinib)
- CBNumber
- CB02630104
- Molecular Formula
- C21H22Cl2N4O2
- Formula Weight
- 433.33
- MOL File
- 869886-67-9.mol
VRT752271 Property
- Boiling point:
- 682.8±55.0 °C(Predicted)
- Density
- 1.359
- storage temp.
- Store at -20°C
- solubility
- DMSO:93.0(Max Conc. mg/mL);214.62(Max Conc. mM)
Ethanol:43.0(Max Conc. mg/mL);99.23(Max Conc. mM) - pka
- 13.34±0.50(Predicted)
- form
- Powder
- color
- White to off-white
- InChIKey
- KSERXGMCDHOLSS-LJQANCHMSA-N
- SMILES
- N1C=C(C2C(Cl)=CN=C(NC(C)C)C=2)C=C1C(N[C@@H](C1=CC=CC(Cl)=C1)CO)=O
Safety
- HS Code
- 2933998090
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
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.
N-Bromosuccinimide Price
- Product number
- CS-2115
- Product name
- Ulixertinib
- Purity
- 99.92%
- Packaging
- 5mg
- Price
- $70
- Updated
- 2021/12/16
- Product number
- FU157994
- Product name
- Ulixertinib
- Packaging
- 10mg
- Price
- $75
- Updated
- 2021/12/16
- Product number
- CS-2115
- Product name
- Ulixertinib
- Purity
- 99.92%
- Packaging
- 10mg
- Price
- $110
- Updated
- 2021/12/16
- Product number
- FU157994
- Product name
- Ulixertinib
- Packaging
- 25mg
- Price
- $125
- Updated
- 2021/12/16
- Product number
- FU157994
- Product name
- Ulixertinib
- Packaging
- 50mg
- Price
- $212.5
- Updated
- 2021/12/16
VRT752271 Chemical Properties,Usage,Production
Uses
Ulixertinib is a potent and reversible ERK1/ERK2 inhibitor with IC50 of <0.3 nM for ERK2. Inhibits cell proliferation. Anti-cancer.
Synthesis
663611-73-2
869886-90-8
869886-67-9
In step 4, a dry and clean 50 L reaction flask was first purged with nitrogen for 20 min to ensure an oxygen-free environment. Subsequently, DMF (30.20 kg) was added to the reactor and stirring was initiated. The reaction temperature was maintained in the range of 15-25 °C and ASYM-112394 (2.76 kg corrected) was slowly added until the solid was completely dissolved. Next, the reaction mixture was cooled to -10 to -20 °C and 1-hydroxybenzotriazole hydrate (2.10 kg) was added at this temperature. Then, EDCI (2.41 kg) was added in five portions at intervals of about 5-10 minutes. The mixture was further cooled to -20 to -30 °C and ASYM-111888 (1.96 kg) was added. Subsequently, DIEA (1.77kg) was added dropwise at a rate of 3-4kg/h. After completion of the addition, the temperature was increased to 15-25°C at a rate of 5-10°C/h and the reaction was maintained at this temperature. During the reaction, samples were taken at 6-8 h intervals and the level of ASYM-112394 was monitored by HPLC until it dropped below 2%. Upon completion of the reaction, the mixture was cooled to 0-10 °C and quenched with a mixture of ethyl acetate (28.80 kg) and water (12.80 kg) pre-cooled to 0-10 °C. Subsequently, the organic phase was separated by extracting with ethyl acetate (28.80 kg) three times, stirring for 20-30 minutes for each extraction and standing for 20-30 minutes. The organic phases were combined and washed twice with purified water (12.80 kg), stirred for 20-30 minutes each time and left to separate. Afterwards, the organic phase was filtered through an in-line fluid filter and the filtrate was transferred to a 300 L glass-lined reactor. The organic phase was washed twice with 5% acetic acid solution (prepared from acetic acid 2.24 kg and water 42.50 kg) at an addition rate of 10-20 kg/h. Next, the organic phase was washed twice with sodium carbonate solution (prepared from sodium carbonate 9.41 kg and water 48.00 kg), and twice with sodium chloride solution (prepared from sodium chloride 16.00 kg and water 44.80 kg). The washed organic phase was transferred to a 300 L glass-lined reactor, anhydrous sodium sulfate (9.70 kg) was added, and stirred at 15-30 °C for 2-4 hours. The mixture was filtered and the filter cake was treated with silica gel (7.50 kg) preloaded with nutche filter and washed with ethyl acetate (14.40 kg). The filtrates were combined and transferred to a 72 L flask through an in-line fluid filter and concentrated under reduced pressure (pressure -0.08 MPa) at 40 °C to a remaining 3-4 L. MTBE (4.78 kg) was added and crystallized by cooling and stirring to 0-10 °C. Samples were taken after 1 h. The percentage by weight of the mother liquor was monitored by gravimetric analysis until it reached 5% or varied by no more than 1% between successive samples. Finally, the product was collected by vacuum filtration and the filter cake was dried under nitrogen protection at 30-40°C to KF ≤ 0.5%, yielding 3.55 kg of off-white solid product with 100% purity. The product was analyzed by XRPD to confirm the structure, and the specific peak positions and intensities are shown in Tables 2 and 3 of the original article.
in vivo
In the pharmacokinetic study, the sensitivity and specificity of the assay are found to be sufficient for accurately characterizing the plasma pharmacokinetics of Ulixertinib (VRT752271) in Balb/C mice[2].
IC 50
ERK2: 0.3 nM (IC50, at KM ATP (60 μM)); ERK1
References
[1] Patent: WO2016/123574, 2016, A1. Location in patent: Paragraph 0233; 0234; 0235; 0236
[2] Patent: WO2016/123581, 2016, A1. Location in patent: Paragraph 146; 0151; 0152; 0153; 0154
[3] Patent: WO2005/113541, 2005, A1. Location in patent: Paragraph 0089
VRT752271 Preparation Products And Raw materials
Raw materials
Preparation Products
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View Lastest Price from VRT752271 manufacturers
- Product
- VRT752271 869886-67-9
- Price
- US $6.68/KG
- Min. Order
- 1KG
- Purity
- 97%-99%
- Supply Ability
- 1kg-1000kg
- Release date
- 2020-01-08