XLI 093

Base Information

• Chemical Name: XLI 093
• CAS No.: 646066-59-3
• Molecular Formula: C₃₃H₂₆N₆O₆
• Molecular Weight: 602.606
• Mol file: 646066-59-3.mol

Synonyms:XLI 093;bis[8-ethynyl-5,6-dihydro-5-methyl-6-oxo-4h-imidazo[1,5-a][1,4]benzodiazepine-3-carboxylic acid]1,3-propanediyl ester hydrate

Chemical Property of XLI 093

Chemical Property:

• PSA: 128.86000
• LogP: 2.47150
• Storage Temp.: 2-8°C
• Solubility.: DMSO: ~16 mg/mL

Purity/Quality:

Xli093 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: Xli 093 is selective α5 GABAA receptor antagonist.

Technology Process of XLI 093

There total 6 articles about XLI 093 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: 73.4%

8-ethynyl-5,6-dihydro-5-methyl-6-oxo-4H-imidazo[1,5-a][1,4]-benzodiazepine-3-carboxylic acid (646066-60-6) + trimethyleneglycol (504-63-2) → XLi-093 (646066-59-3)

Guidance literature:

8-ethynyl-5,6-dihydro-5-methyl-6-oxo-4H-imidazo[1,5-a][1,4]-benzodiazepine-3-carboxylic acid; With 1,1'-carbonyldiimidazole; In N,N-dimethyl-formamide; at 20 ℃; for 2h;

trimethyleneglycol; With 1,8-diazabicyclo[5.4.0]undec-7-ene; In N,N-dimethyl-formamide; at 20 ℃; for 4.5h;

DOI:10.1021/jm034164c

Reference yield:

7-bromo-3,4-dihydro-4-methyl-2H-1,4-benzodiazepine-2,5-(1H)-dione (78756-36-2) → XLi-093 (646066-59-3)

Guidance literature:

Multi-step reaction with 5 steps

1.1: LDA; ClPO(OEt)2 / tetrahydrofuran / 0 °C

1.2: 40 percent / LDA / tetrahydrofuran

2.1: 80 percent / Pd(OAc)2(PPh₃)2; Et₃N / acetonitrile / Heating

3.1: 88 percent / aq. TBAF / tetrahydrofuran / 20 °C

4.1: 90 percent / aq. NaOH / ethanol / 70 °C

5.1: carbonyl diimidazole / dimethylformamide / 2 h / 20 °C

5.2: 73.4 percent / DBU / dimethylformamide / 4.5 h / 20 °C

With sodium hydroxide; bis(triphenylphosphine) palladium (Il) acetate; tetrabutyl ammonium fluoride; diethyl chlorophosphate; triethylamine; 1,1'-carbonyldiimidazole; lithium diisopropyl amide; In tetrahydrofuran; ethanol; N,N-dimethyl-formamide; acetonitrile; 2.1: Heck-type coupling;

DOI:10.1021/jm034164c

Reference yield:

4-methyl-3H-1,4-benzodiazepine-2,5-(1H,4H)-dione (3415-35-8) → XLi-093 (646066-59-3)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 80 percent / Br₂; NaOAc; AcOH / 20 °C

2.1: LDA; ClPO(OEt)2 / tetrahydrofuran / 0 °C

2.2: 40 percent / LDA / tetrahydrofuran

3.1: 80 percent / Pd(OAc)2(PPh₃)2; Et₃N / acetonitrile / Heating

4.1: 88 percent / aq. TBAF / tetrahydrofuran / 20 °C

5.1: 90 percent / aq. NaOH / ethanol / 70 °C

6.1: carbonyl diimidazole / dimethylformamide / 2 h / 20 °C

6.2: 73.4 percent / DBU / dimethylformamide / 4.5 h / 20 °C

With sodium hydroxide; bis(triphenylphosphine) palladium (Il) acetate; tetrabutyl ammonium fluoride; bromine; sodium acetate; diethyl chlorophosphate; acetic acid; triethylamine; 1,1'-carbonyldiimidazole; lithium diisopropyl amide; In tetrahydrofuran; ethanol; N,N-dimethyl-formamide; acetonitrile; 3.1: Heck-type coupling;

DOI:10.1021/jm034164c

upstream raw materials:

8-ethynyl-5,6-dihydro-5-methyl-6-oxo-4H-imidazo[1,5-a][1,4]-benzodiazepine-3-carboxylic acid

trimethyleneglycol

7-bromo-3,4-dihydro-4-methyl-2H-1,4-benzodiazepine-2,5-(1H)-dione

4-methyl-3H-1,4-benzodiazepine-2,5-(1H,4H)-dione

Refernces

• 1、 Han, Dongmei,Holger Foersterling,Li, Xiaoyan,Deschamps, Jeffrey R.,Parrish, Damon,Cao, Hui,Rallapalli, Sundari,Clayton, Terry,Teng, Yun,Majumder, Samarpan,Sankar, Subramaniam,Roth, Bryan L.,Sieghart, Werner,Furtmuller, Roman,Rowlett, James K.,Weed, Michael R.,Cook, James M.. "A study of the structure-activity relationship of GABAA-benzodiazepine receptor bivalent ligands by conformational analysis with low temperature NMR and X-ray analysis". experimental part. p. 8853 - 8862. Retrieved 2009/04/11.