A77 1726

Base Information

• Chemical Name: A77 1726
• CAS No.: 108605-62-5
• Molecular Formula: C₁₂H₉F₃N₂O₂
• Molecular Weight: 270.211
• Hs Code.: 2926900005
• Mol file: 108605-62-5.mol

Synonyms:2-Cyano-3-hydroxy-N-(4-trifluoromethylphenyl)crotonamide;2-Cyano-3-hydroxy-N-[4-(trifluoromethyl)phenyl]but-2-enamide; Malononitrilamide

Chemical Property of A77 1726

Chemical Property:

• Appearance/Colour: White solid.
• Vapor Pressure: 6.63E-06mmHg at 25°C
• Melting Point: 229-232°C
• Boiling Point: 410.8 °C at 760 mmHg
• PKA: 5.20±0.50(Predicted)
• Flash Point: 202.3 °C
• PSA: 73.12000
• Density: 1.424 g/cm³
• LogP: 3.07248
• Storage Temp.: +2C to +8C
• Solubility.: Soluble in DMSO (up to 30 mg/ml), or in Ethanol (up to 5 mg/ml with warming).

Purity/Quality:

99% ^*data from raw suppliers

Teriflunomide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22

MSDS Files:

SDS file from LookChem

Useful:

• Description: Teriflunomide (Aubagio?), also known as A77 1726, is an immunosupressant marketed by Sanofi for the teatment of multiple sclerosis (MS). Teriflunomide is the active metabolite of leflunomide, used for treatment of patients diagnosed with rheumatoid arthritis, and therefore simultaneously can be used as a treatment for rheumatoid arthritis.Teriflunomide acts as an inhibitor of the mitochondrial enzyme dihydrorotate dehydrogenase, inhibiting pyrimidine formation, and resulting in reduced B and T cell proliferation.
• Uses: The active metabolite of Leflunomide, 2-Cyano-3-hydroxy-N-(4'-trifluoromethylphenyl)-crotone amide can be used as a potent disease-modifying antirheumatic drug used in the treatment of rheumatoid arthritis.
• Clinical Use: Immunomodulating agent: Treatment of relapsing remitting multiple sclerosis
• Drug interactions: Potentially hazardous interactions with other drugs Lipid-lowering agents: effect significantly reduced by colestyramine - avoid; concentration of rosuvastatin increased - consider reducing rosuvastatin dose. Live vaccines: risk of generalised infections - avoid.

Technology Process of A77 1726

There total 14 articles about A77 1726 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: 95.0%

Leflunomide (75706-12-6) → teriflunomide (163451-81-8,108605-62-5)

Guidance literature:

Leflunomide; With sodium hydroxide; In water; isopropyl alcohol; at 30 ℃; pH=12;

With hydrogenchloride; at 30 ℃;

Reference yield: 92.0%

2-cyano-N-(4-trifluoromethylphenyl)acetamide (24522-30-3) + acetic anhydride (108-24-7) → teriflunomide (163451-81-8,108605-62-5)

Guidance literature:

2-cyano-N-(4-trifluoromethylphenyl)acetamide; With sodium hydroxide; In water; acetone; at 15 ℃;

acetic anhydride; In water; acetone; at 15 ℃; for 8.5h;

With hydrogenchloride; In water; at 5 - 10 ℃; for 2h; Product distribution / selectivity;

Reference yield: 88.3%

2-cyano-N-(4-trifluoromethylphenyl)acetamide (24522-30-3) + acetyl chloride (75-36-5) → teriflunomide (163451-81-8,108605-62-5)

Guidance literature:

2-cyano-N-(4-trifluoromethylphenyl)acetamide; With sodium hydride; In acetonitrile; for 0.166667h;

acetyl chloride; In acetonitrile; at 25 ℃; Cooling;

upstream raw materials:

Leflunomide

sodium cyanide

2-bromo-3-oxo-N-[4-(trifluoromethyl)phenyl]butanamide

5-methyl-1,2-oxazole-4-carboxylic acid

Refernces

• 1、 . "Kemp Eliminases of the AlleyCat Family Possess High Substrate Promiscuity". . p. 1425 - 1430. Retrieved 2019.
• 2、 -. "Simple preparation method of teriflunomide". Paragraph 0063; 0069-0071; 0072; 0076-0077; 0078; 0082; .... . Retrieved 2021/07/08.
• 3、 -. "Preparation method of teriflunomide". Paragraph 0051-0077. . Retrieved 2020/04/02.