diethyl 2-{[(1,3-dimethyl-1H-pyrazol-5-yl)amino]methylidene}malonate

Base Information

• Chemical Name: diethyl 2-{[(1,3-dimethyl-1H-pyrazol-5-yl)amino]methylidene}malonate
• CAS No.: 20481-33-8
• Molecular Formula: C₁₃H₁₉N₃O₄
• Molecular Weight: 281.312
• Hs Code.: 2933199090
• DSSTox Substance ID: DTXSID50381033
• Mol file: 20481-33-8.mol

Synonyms:20481-33-8;diethyl 2-{[(1,3-dimethyl-1H-pyrazol-5-yl)amino]methylidene}malonate;Diethyl 2-(((1,3-dimethyl-1H-pyrazol-5-yl)amino)methylene)malonate;diethyl 2-[[(2,5-dimethylpyrazol-3-yl)amino]methylidene]propanedioate;Diethyl 2-((1,3-dimethyl-1H-pyrazol-5-ylamino)methylene)malonate;1,3-diethyl 2-{[(1,3-dimethyl-1H-pyrazol-5-yl)amino]methylidene}propanedioate;Diethyl 2-([(1,3-dimethyl-1H-pyrazol-5-yl)amino]methylidene)malonate;SCHEMBL582277;DTXSID50381033;MFCD00067953;diethyl {[(1,3-dimethyl-1h-pyrazol-5-yl)amino]methylidene}propanedioate;AS-9182;CCG-249742;CS-0328358;FT-0624824;A814596;diethyl 2-[[(2,5-dimethylpyrazol-3-yl)amino]methylene]propanedioate;Diethyl 2-([(1,3-dimethyl-1H-pyrazol-5-yl)amino]methylidene) malonate;Diethyl2-{[(1,3-dimethyl-1H-pyrazol-5-yl)amino]methylidene}malonate

Chemical Property of diethyl 2-{[(1,3-dimethyl-1H-pyrazol-5-yl)amino]methylidene}malonate

Chemical Property:

• Vapor Pressure: 1.43E-05mmHg at 25°C
• Melting Point: 85℃
• Boiling Point: 366.7°Cat760mmHg
• Flash Point: 175.6°C
• PSA: 82.45000
• Density: 1.18g/cm³
• LogP: 1.22350
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 8
• Exact Mass: 281.13755610
• Heavy Atom Count: 20
• Complexity: 364

Purity/Quality:

98%min ^*data from raw suppliers

Diethyl 2-{[(1,3-dimethyl-1H-pyrazol-5-yl)amino]methylidene}malonate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): R36/37/38:Irritating to eyes, respiratory system and skin.
• Hazard Codes: Xi:Irritant
• Statements: R36/37/38:Irritating to eyes, respiratory system and skin.
• Safety Statements: S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.; S37/39:Wear suitable g

MSDS Files:

Useful:

• Canonical SMILES: CCOC(=O)C(=CNC1=CC(=NN1C)C)C(=O)OCC

Technology Process of diethyl 2-{[(1,3-dimethyl-1H-pyrazol-5-yl)amino]methylidene}malonate

There total 2 articles about diethyl 2-{[(1,3-dimethyl-1H-pyrazol-5-yl)amino]methylidene}malonate 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: 89.0%

5-Amino-1,3-dimethylpyrazole (3524-32-1) + diethyl 2-ethoxymethylenemalonate (87-13-8) → diethyl 2-{[(1,3-dimethyl-1H-pyrazol-5-yl)amino]methylene}malonate (20481-33-8)

Guidance literature:

at 120 ℃;

DOI:10.1016/j.bmcl.2003.10.025

Reference yield:

→ diethyl 2-{[(1,3-dimethyl-1H-pyrazol-5-yl)amino]methylene}malonate (20481-33-8)

Guidance literature:

Reference yield:

diethyl 2-{[(1,3-dimethyl-1H-pyrazol-5-yl)amino]methylene}malonate (20481-33-8) → 4-anilino-1,3-dimethyl-1H-pyrazolo[3,4-b]pyridine-5-carboxamide

Guidance literature:

Multi-step reaction with 5 steps

1: 77 percent / POCl₃ / 18 h / 120 °C

2: 99 percent / potassium hydroxide / H₂O; 1,2-dimethoxy-ethane / 18 h / 20 °C

3: SOCl₂ / 1 h / 80 °C

4: 1.98 g / aq. ammonium / tetrahydrofuran / 0.17 h / 0 °C

5: 63 percent / dioxane / 1 h / 120 °C

With potassium hydroxide; ammonium hydroxide; thionyl chloride; trichlorophosphate; In tetrahydrofuran; 1,4-dioxane; 1,2-dimethoxyethane; water;

DOI:10.1016/j.bmc.2004.05.032

upstream raw materials:

5-Amino-1,3-dimethylpyrazole

diethyl 2-ethoxymethylenemalonate

Downstream raw materials:

ethyl 4-chloro-1,3-dimethylpyrazolo[3,4-b]pyridine-5-carboxylate

4-Chloro-1,3-dimethyl-1H-pyrazolo[3,4-b]pyridine-5-carbonyl chloride

4-chloro-1,3-dimethyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid

4-chloro-1,3-dimethyl-1H-pyrazolo[3,4-b]pyridine-5-carboxamide

Refernces

• 1、 Aghazadeh Tabrizi, Mojgan,Baraldi, Pier Giovanni,Saponaro, Giulia,Moorman, Allan R.,Romagnoli, Romeo,Preti, Delia,Baraldi, Stefania,Corciulo, Carmen,Vincenzi, Fabrizio,Borea, Pier Andrea,Varani, Katia. "Design, synthesis, and pharmacological properties of new heteroarylpyridine/heteroarylpyrimidine derivatives as CB2 cannabinoid receptor partial agonists". . p. 1098 - 1112. Retrieved 2013/03/28.
• 2、 -. "PYRAZOLO [3, 4-B] PYRIDINE DERIVATIVES AS PHOSPHODIESTERASE INHIBITORS". Page/Page column 53. . Retrieved 2008/12/07.