BMS 833923

Base Information

• Chemical Name: BMS 833923
• CAS No.: 1059734-66-5
• Molecular Formula: C30H27N5O
• Molecular Weight: 473.577
• Mol file: 1059734-66-5.mol

Synonyms:S7138,XL139;N-{2-methyl-5-[(methylamino)methyl]phenyl}-4-[(4-phenylquinazolin-2-yl)amino]benzamide;

Chemical Property of BMS 833923

Chemical Property:

• PKA: 13.42±0.70(Predicted)
• PSA: 78.94000
• Density: 1.252±0.06 g/cm3(Predicted)
• LogP: 6.85740
• Solubility.: ≥47.4 mg/mL in DMSO; insoluble in H2O; ≥5.14 mg/mL in EtOH with gentle warming and ultrasonic

Purity/Quality:

99% ^*data from raw suppliers

BMS833923 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: Smoothened (Smo) is a cell surface receptor that, with Patched, mediates sonic hedgehog (Shh) signaling to regulate gene expression through the Gli transcription factors. BMS 833923 is an orally bioavailable inhibitor of Smo. It blocks binding of BODIPY cyclopamine (IC50 = 21 nM) and inhibits Gli activation in cell lines that express wild-type Smo or activated mutant forms of Smo (IC50s = 6-35 nM). BMS 833923 robustly inhibits Shh pathway activity and prevents tumor growth in medulloblastoma and pancreatic carcinoma xenograft models.

Technology Process of BMS 833923

There total 7 articles about BMS 833923 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: 57.0%

N-(5-chloromethyl-2-methylphenyl)-4-(4-phenylquinazolin-2-ylamino)benzamide (1059735-25-9) + methylamine (74-89-5) → BMS-833923 (1059734-66-5)

Guidance literature:

In tetrahydrofuran; at 0 - 20 ℃;

Reference yield:

2-chloro-4-phenylquinazoline (29874-83-7) → BMS-833923 (1059734-66-5)

Guidance literature:

Multi-step reaction with 5 steps

1: isopropyl alcohol / 4 h / Heating / reflux

2: thionyl chloride / N,N-dimethyl-formamide / dichloromethane / 20 °C

3: triethylamine / dichloromethane / 0 - 20 °C

4: thionyl chloride / dichloromethane / 2 h / 0 °C

5: tetrahydrofuran / 0 - 20 °C

With thionyl chloride; triethylamine; N,N-dimethyl-formamide; In tetrahydrofuran; dichloromethane; isopropyl alcohol;

Reference yield:

4-phenyl-1H-quinazolin-2-one (23441-75-0) → BMS-833923 (1059734-66-5)

Guidance literature:

Multi-step reaction with 6 steps

1: trichlorophosphate / 0.5 h / 105 °C

2: isopropyl alcohol / 4 h / Heating / reflux

3: thionyl chloride / N,N-dimethyl-formamide / dichloromethane / 20 °C

4: triethylamine / dichloromethane / 0 - 20 °C

5: thionyl chloride / dichloromethane / 2 h / 0 °C

6: tetrahydrofuran / 0 - 20 °C

With thionyl chloride; triethylamine; trichlorophosphate; N,N-dimethyl-formamide; In tetrahydrofuran; dichloromethane; isopropyl alcohol;

upstream raw materials:

N-(5-chloromethyl-2-methylphenyl)-4-(4-phenylquinazolin-2-ylamino)benzamide

methylamine

4-phenyl-1H-quinazolin-2-one

2-chloro-4-phenylquinazoline

Refernces