ZA7371

Base Information

• Chemical Name: ZA7371
• CAS No.: 1494675-86-3
• Molecular Formula: C18H21N5O3
• Molecular Weight: 355.39
• Mol file: 1494675-86-3.mol

Synonyms:ZA7371;DprE1-IN-1;AZ-7371;N-(2-Hydroxyethyl)-1-[(6-methoxy-5-methylpyrimidin-4-yl)methyl]-6-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide;DprE1-IN-1 ZA7371

Chemical Property of ZA7371

Chemical Property:

• Boiling Point: 691.6±55.0 °C(Predicted)
• PKA: 12.79±0.46(Predicted)
• PSA: 102.16000
• Density: 1.34±0.1 g/cm3(Predicted)
• LogP: 1.61300

Purity/Quality:

98% min ^*data from raw suppliers

AZ-7371（DprE1-IN-1） >98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ZA7371

There total 7 articles about ZA7371 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: 53.0%

1-((6-methoxy-5-methylpyrimidin-4-yl)methyl)-6-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxylic acid (1494676-19-5) + ethanolamine (141-43-5) → N-(2-hydroxyethyl)-1-((6-methoxy-5-methylpyrimidin-4-yl)-methyl)-6-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide (1494675-86-3)

Guidance literature:

1-((6-methoxy-5-methylpyrimidin-4-yl)methyl)-6-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxylic acid; With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine; In dichloromethane; at 20 ℃; for 0.0833333h;

ethanolamine; In dichloromethane; at 20 ℃;

DOI:10.1128/AAC.03233-14

Reference yield:

2-(5-Methyl-3-nitro-pyridin-2-yl)-malonic acid diethyl ester (533910-47-3) → N-(2-hydroxyethyl)-1-((6-methoxy-5-methylpyrimidin-4-yl)-methyl)-6-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide (1494675-86-3)

Guidance literature:

Multi-step reaction with 6 steps

1.1: lithium chloride / dimethyl sulfoxide; water / 16 h / 80 °C / Inert atmosphere

2.1: N,N-dimethyl acetamide / 16 h / 80 °C / Inert atmosphere

3.1: acetic acid; iron / 2 h / 60 °C / Inert atmosphere

4.1: potassium carbonate / N,N-dimethyl-formamide / 3 h / 80 °C / Inert atmosphere

5.1: lithium hydroxide / water; ethanol / 5 h / 20 °C / Inert atmosphere

6.1: triethylamine; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide / dichloromethane / 0.08 h / 20 °C / Inert atmosphere

6.2: 20 °C / Inert atmosphere

With iron; potassium carbonate; acetic acid; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine; lithium chloride; lithium hydroxide; In ethanol; dichloromethane; N,N-dimethyl acetamide; water; dimethyl sulfoxide; N,N-dimethyl-formamide;

DOI:10.1021/jm401382v

Reference yield:

2-chloro-5-methyl-3-nitro-pyridine (23056-40-8) → N-(2-hydroxyethyl)-1-((6-methoxy-5-methylpyrimidin-4-yl)-methyl)-6-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide (1494675-86-3)

Guidance literature:

Multi-step reaction with 7 steps

1.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / Inert atmosphere

1.2: 4 h / 20 - 80 °C / Inert atmosphere

2.1: lithium chloride / dimethyl sulfoxide; water / 16 h / 80 °C / Inert atmosphere

3.1: N,N-dimethyl acetamide / 16 h / 80 °C / Inert atmosphere

4.1: acetic acid; iron / 2 h / 60 °C / Inert atmosphere

5.1: potassium carbonate / N,N-dimethyl-formamide / 3 h / 80 °C / Inert atmosphere

6.1: lithium hydroxide / water; ethanol / 5 h / 20 °C / Inert atmosphere

7.1: triethylamine; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide / dichloromethane / 0.08 h / 20 °C / Inert atmosphere

7.2: 20 °C / Inert atmosphere

With iron; sodium hydride; potassium carbonate; acetic acid; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine; lithium chloride; lithium hydroxide; In ethanol; dichloromethane; N,N-dimethyl acetamide; water; dimethyl sulfoxide; N,N-dimethyl-formamide;

DOI:10.1021/jm401382v

upstream raw materials:

1-((6-methoxy-5-methylpyrimidin-4-yl)methyl)-6-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxylic acid

ethanolamine

2-(5-Methyl-3-nitro-pyridin-2-yl)-malonic acid diethyl ester

2-chloro-5-methyl-3-nitro-pyridine

Refernces

• 1、 -. "AZAINDOLE COMPOUNDS, SYNTHESIS THEREOF, AND METHODS OF USING THE SAME". Paragraph 0168; 0297; 0298. . Retrieved 2015/02/18.
• 2、 Shirude, Pravin S.,Shandil, Radha,Sadler, Claire,Naik, Maruti,Hosagrahara, Vinayak,Hameed, Shahul,Shinde, Vikas,Bathula, Chandramohan,Humnabadkar, Vaishali,Kumar, Naveen,Reddy, Jitendar,Panduga, Vijender,Sharma, Sreevalli,Ambady, Anisha,Hegde, Naina,Whiteaker, James,McLaughlin, Robert E.,Gardner, Humphrey,Madhavapeddi, Prashanti,Ramachandran, Vasanthi,Kaur, Parvinder,Narayan, Ashwini,Guptha, Supreeth,Awasthy, Disha,Narayan, Chandan,Mahadevaswamy, Jyothi,Vishwas,Ahuja, Vijaykamal,Srivastava, Abhishek,Prabhakar, Kr,Bharath, Sowmya,Kale, Ramesh,Ramaiah, Manjunatha,Choudhury, Nilanjana Roy,Sambandamurthy, Vasan K.,Solapure, Suresh,Iyer, Pravin S.,Narayanan, Shridhar,Chatterji, Monalisa. "Azaindoles: Noncovalent DprE1 inhibitors from scaffold morphing efforts, kill Mycobacterium tuberculosis and are efficacious in vivo". . p. 9701 - 9708. Retrieved 2014/01/06.