LY2940680

Base Information

• Chemical Name: LY2940680
• CAS No.: 1258861-20-9
• Molecular Formula: C26H24F4N6O
• Molecular Weight: 512.51
• Mol file: 1258861-20-9.mol

Synonyms:4-Fluoro-N-methyl-N-[1-[4-(1-methyl-1H-pyrazol-5-yl)-1-phthalazinyl]-4-piperidinyl]-2-(trifluoromethyl)benzamide;

Chemical Property of LY2940680

Chemical Property:

• Boiling Point: 703.5±60.0 °C(Predicted)
• PKA: 7.94±0.30(Predicted)
• PSA: 67.15000
• Density: 1.39
• LogP: 4.99420
• Solubility.: insoluble in H2O; ≥5.2 mg/mL in EtOH with ultrasonic; ≥51.3 mg/mL in DMSO with gentle warming and ultrasonic

Purity/Quality:

98% min ^*data from raw suppliers

LY2940680 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Smoothened (Smo) is a GPCR-like receptor that, with Patched, mediates hedgehog (Hh) signaling to regulate gene expression through the Gli transcription factors. LY2940680 is an antitumor agent that binds to the human Smo receptor and inhibits Sonic Hh-induced Gli1 expression (IC50 = ~2.4 nM in vitro). The potential anticancer activity of LY2940680 is currently under clinical investigation.[Cayman Chemical] LY2940680 binds to the Smoothened (Smo) receptor and potently inhibits Hedgehog (Hh) signaling.

Technology Process of LY2940680

There total 7 articles about LY2940680 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: 92.0%

N-[1-(4-chloro-phthalazin-1-yl)-piperidin-4-yl]-4-fluoro-N-methyl-2-trifluoromethyl-benzamide + 1-methyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole (847818-74-0) → 4-fluoro-N-methyl-N-{1-[4-(1-methyl-1H-pyrazole-5-yl)phthalazin-1-yl]piperidin-4-yl}-2-(trifluoromethyl)benzamide (1258861-20-9)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate; In ethanol; water; toluene; at 74 ℃; for 12h; Inert atmosphere;

DOI:10.3184/003685017X14859543105069

Reference yield: 86.0%

N-methyl-1-[4-(2-methylpyrazol-3-yl)phthalazin-1-yl]piperidin-4-amine (1258861-50-5) + 2-trifluoromethyl-4-fluorobenzoyl chloride (189807-21-4) → 4-fluoro-N-methyl-N-{1-[4-(1-methyl-1H-pyrazole-5-yl)phthalazin-1-yl]piperidin-4-yl}-2-(trifluoromethyl)benzamide (1258861-20-9)

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃; for 3h;

Reference yield:

1-benzyl-N-methylpiperidin-4-amine (7006-50-0) → 4-fluoro-N-methyl-N-{1-[4-(1-methyl-1H-pyrazole-5-yl)phthalazin-1-yl]piperidin-4-yl}-2-(trifluoromethyl)benzamide (1258861-20-9)

Guidance literature:

Multi-step reaction with 4 steps

1: triethylamine / dichloromethane / 6 h / 20 °C

2: ammonium formate; palladium on activated charcoal / methanol / 12 h / 50 °C / Inert atmosphere

3: potassium carbonate / 12 h / 80 °C

4: sodium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / toluene; ethanol; water / 12 h / 74 °C / Inert atmosphere

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; palladium on activated charcoal; ammonium formate; sodium carbonate; potassium carbonate; triethylamine; In methanol; ethanol; dichloromethane; water; toluene; 4: |Suzuki Coupling;

DOI:10.3184/003685017X14859543105069

upstream raw materials:

N-methyl-1-[4-(2-methylpyrazol-3-yl)phthalazin-1-yl]piperidin-4-amine

2-trifluoromethyl-4-fluorobenzoyl chloride

1-methyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole

1-phenylmethyl-4-piperidone

Refernces

• 1、 -. "Synthetic method of Taladegib". Paragraph 0037; 0061; 0062. . Retrieved 2017/08/25.