BI-7273

Base Information

• Chemical Name: BI-7273
• CAS No.: 1883429-21-7
• Molecular Formula: C₂₀H₂₃N₃O₃
• Molecular Weight: 353.421
• Mol file: 1883429-21-7.mol

Synonyms:

Chemical Property of BI-7273

Chemical Property:

• Boiling Point: 509.2±50.0 °C(Predicted)
• PKA: 8.32±0.28(Predicted)
• Density: 1.189±0.06 g/cm3(Predicted)
• Solubility.: ≥35.3 mg/mL in DMSO with gentle warming; ≥1.99 mg/mL in EtOH with ultrasonic; ≥8.74 mg/mL in H2O

Purity/Quality:

99% ^*data from raw suppliers

BI-7273 >98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Description: BI-7273 is a potent BRD9 bromodomain inhibitor (Kd = 15.4 nM; IC50 = 19 nM) that less effectively inhibits the functionally and structurally related BRD7 bromodomain (IC50 = 117 nM). It is without effect against the bromodomains of BRD2 and BRD4, as well as a panel of kinases. BI-7273 inhibits the growth of EOL-1 acute myeloid leukemia cells in vitro (EC50 = 1.4 μM).

Technology Process of BI-7273

There total 8 articles about BI-7273 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: 76.48%

2,6-dimethoxy-4-(2-methyl-1-oxo-1,2-dihydro-2,7-naphthyridin-4-yl)benzaldehyde + dimethyl amine (124-40-3) → 4-{4-[(dimethylamino)methyl]-3,5-dimethoxyphenyl}-2-methyl-1,2-dihydro-2,7-naphthyridin-1-one (1883429-21-7)

Guidance literature:

With sodium cyanoborohydride; In methanol; at 20 ℃; for 2h;

Reference yield: 71.0%

4-bromo-2-methyl-1,2-dihydro-2,7-naphthyridin-1-one (1706749-51-0) + {[2,6-dimethoxy-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methyl}dimethylamine hydrochloride → 4-{4-[(dimethylamino)methyl]-3,5-dimethoxyphenyl}-2-methyl-1,2-dihydro-2,7-naphthyridin-1-one (1883429-21-7)

Guidance literature:

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; sodium carbonate; In N,N-dimethyl-formamide; at 80 ℃; for 1h; Inert atmosphere;

DOI:10.1021/acs.jmedchem.5b01865

Reference yield:

4-bromo-1,2-dihydro-2,7-naphthyridin-1-one (959558-27-1) → 4-{4-[(dimethylamino)methyl]-3,5-dimethoxyphenyl}-2-methyl-1,2-dihydro-2,7-naphthyridin-1-one (1883429-21-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium hydride / N,N-dimethyl-formamide / 0 °C

1.2: 20 - 25 °C

2.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; sodium carbonate / N,N-dimethyl-formamide / 1 h / 80 °C / Inert atmosphere

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; sodium hydride; sodium carbonate; In N,N-dimethyl-formamide;

DOI:10.1021/acs.jmedchem.5b01865

upstream raw materials:

4-bromo-1,2-dihydro-2,7-naphthyridin-1-one

4-bromo-2-methyl-1,2-dihydro-2,7-naphthyridin-1-one

4-bromo-2,6-dimethoxy-benzaldehyde

dimethyl amine