UNC2025

Base Information

• Chemical Name: UNC2025
• CAS No.: 1429881-91-3
• Molecular Formula: C₂₈H₄₀N₆O
• Molecular Weight: 476.665
• Mol file: 1429881-91-3.mol

Synonyms:UNC2025;(1R,4R)-4-(2-(butylamino)-5-(4-((4-methylpiperazin-1-yl)methyl)phenyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)cyclohexanol UNC-2025;mrx-6313;trans-4-(2-(Butylamino)-5-(4-((4-methylpiperazin-1-yl)methyl)phenyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)cyclohexanol;trans-4-[2-(Butylamino)-5-[4-[(4-methyl-1-piperazinyl)methyl]phenyl]-7H-pyrrolo[2,3-d]pyrimidin-7-yl]cyclohexanol

Chemical Property of UNC2025

Chemical Property:

• PSA: 69.45000
• LogP: 4.48250
• Solubility.: ≥23.85 mg/mL in DMSO; insoluble in EtOH; ≥6.09 mg/mL in H2O with ultrasonic

Purity/Quality:

99%, ^*data from raw suppliers

UNC 2025 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Description: UNC2025 is a potent, orally bioavailable inhibitor of the tyrosine kinases Mer and Flt3 (IC50s = 0.74 and 0.80 nM, respectively). It less potently inhibits Axl and Tyro3 (IC50s = 14 and 17 nM, respectively) and a panel of related kinases. UNC2025 blocks colony formation of Mer- and Flt3-dependent tumor cell lines and inhibits Mer phosphorylation in bone marrow leukemia cells in vivo. Pharmacokinetic studies suggest that orally administered UNC2025 at 3 mg/kg will suffice to provide 90% inhibition of Mer and Flt3 at 30 min.
• Uses: UNC 2025 is Mer/FLT3 dual inhibitor. It can be used in biological study. Novel MERTK inhibitor UNC2025 induced polyploidy and promoted death and senescence in human glioblastoma multiforme cells where high levels of GAS6 MERTK ligand expression correlated with decreased overall survival in patients.

Technology Process of UNC2025

There total 10 articles about UNC2025 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: 89.0%

N-butyl-7-(trans-4-((tert-butyldimethylsilyl)oxy)cyclohexyl)-5-(4-((4-methylpiperazin-1-yl)methyl)phenyl)-7H-pyrrolo[2,3-d]pyrimidin-2-amine → trans-4-(2-(butylamino)-5-(4-((4-methylpiperazin-1-yl)methyl)phenyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)cyclohexan-1-ol (1429881-91-3)

Guidance literature:

With hydrogenchloride; In 1,4-dioxane; methanol; dichloromethane; at 20 ℃; for 2h;

DOI:10.1021/jm500749d

Reference yield:

7-(trans-4-((tert-butyldimethylsilyl)oxy)cyclohexyl)-2-chloro-7H-pyrrolo[2,3-d]pyrimidine (1621619-13-3) → trans-4-(2-(butylamino)-5-(4-((4-methylpiperazin-1-yl)methyl)phenyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)cyclohexan-1-ol (1429881-91-3)

Guidance literature:

Multi-step reaction with 4 steps

1: N-Bromosuccinimide / N,N-dimethyl-formamide / 20 °C

2: N-ethyl-N,N-diisopropylamine / isopropyl alcohol / 95 °C

3: tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate / water; 1,4-dioxane / 2 h / 90 °C

4: hydrogenchloride / methanol; 1,4-dioxane; dichloromethane / 2 h / 20 °C

With hydrogenchloride; N-Bromosuccinimide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate; N-ethyl-N,N-diisopropylamine; In 1,4-dioxane; methanol; dichloromethane; water; N,N-dimethyl-formamide; isopropyl alcohol; 3: |Suzuki-Miyaura Coupling;

DOI:10.1021/jm500749d

Reference yield:

trans-4-((5-bromo-2-chloropyrimidin-4-yl)amino)cyclohexan-1-ol → trans-4-(2-(butylamino)-5-(4-((4-methylpiperazin-1-yl)methyl)phenyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)cyclohexan-1-ol (1429881-91-3)

Guidance literature:

Multi-step reaction with 7 steps

1: copper(l) iodide; triethylamine; bis-triphenylphosphine-palladium(II) chloride; triphenylphosphine / toluene / 2.5 h / 60 °C / Inert atmosphere

2: tetrabutyl ammonium fluoride / tetrahydrofuran / 5 h / 65 °C

3: 1H-imidazole / N,N-dimethyl-formamide / 1 h / 0 - 20 °C

4: N-Bromosuccinimide / N,N-dimethyl-formamide / 20 °C

5: N-ethyl-N,N-diisopropylamine / isopropyl alcohol / 95 °C

6: tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate / water; 1,4-dioxane / 2 h / 90 °C

7: hydrogenchloride / methanol; 1,4-dioxane; dichloromethane / 2 h / 20 °C

With 1H-imidazole; hydrogenchloride; bis-triphenylphosphine-palladium(II) chloride; N-Bromosuccinimide; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; tetrabutyl ammonium fluoride; potassium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; N,N-dimethyl-formamide; isopropyl alcohol; toluene; 1: |Sonogashira Cross-Coupling / 6: |Suzuki-Miyaura Coupling;

DOI:10.1021/jm500749d

upstream raw materials:

trans-4-(2-chloro-7H-pyrrolo[2,3-d]pyrimidin-7-yl)cyclohexan-1-ol

7-(trans-4-((tert-butyldimethylsilyl)oxy)cyclohexyl)-2-chloro-7H-pyrrolo[2,3-d]pyrimidine

trans-4-hydroxycyclohexylamine

5-bromo-2-chloro-7H-pyrrolo[2,3-d]pyrimidine

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