Repirinast

Base Information

• Chemical Name: Repirinast
• CAS No.: 73080-51-0
• Molecular Formula: C₂₀H₂₁NO₅
• Molecular Weight: 355.39
• Hs Code.: 2934999090
• UNII: 4K8KA8B61G
• DSSTox Substance ID: DTXSID10223349
• Nikkaji Number: J22.795A
• Wikipedia: Repirinast
• Wikidata: Q7314016
• NCI Thesaurus Code: C73053
• ChEMBL ID: CHEMBL2105300
• Mol file: 73080-51-0.mol

Synonyms:isoamyl 5,6-dihydro-7,8-dimethyl-4,5-dioxo-4H-pyrano(3,2-C)quinoline -2-carboxylate;MY 5116;MY-5116;repirinast

Chemical Property of Repirinast

Chemical Property:

• Vapor Pressure: 1.67E-13mmHg at 25°C
• Melting Point: 236-241°
• Refractive Index: 1.6000 (estimate)
• Boiling Point: 581.3°C at 760 mmHg
• Flash Point: 305.4°C
• PSA: 89.37000
• Density: 1.27g/cm³
• LogP: 3.45420
• Storage Temp.: 2-8°C
• Solubility.: DMSO (Sparingly, Heated), Methanol (Slightly, Heated)
• Water Solubility.: 1.2mg/L(temperature not stated)
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 355.14197277
• Heavy Atom Count: 26
• Complexity: 690

Purity/Quality:

98%,99%, ^*data from raw suppliers

Repirinast(>80%) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C2=C(C=C1)C3=C(C(=O)C=C(O3)C(=O)OCCC(C)C)C(=O)N2)C
• Description: Repirinast is an orally-active antiallergic agent useful in the treatment of allergic asthma. Its activity is reportedly attributed to a metabolite, the corresponding free acid (MY-1250), which is 17 times more potent than disodium cromoglycate in inhibiting histamine release due to antigen-antibody reactions.

Technology Process of Repirinast

There total 5 articles about Repirinast 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:

3-acetyl-4-hydroxy-7,8-dimethyl-2-quinolone (63768-46-7) → repirinast (73080-51-0)

Guidance literature:

Multi-step reaction with 4 steps

1: sodium ethylate / benzene / 2 h / Heating

2: conc. hydrochloric acid / acetic acid / 0.67 h / 100 °C

3: thionyl chloride / 7 h / Heating

4: 2 h / Heating

With hydrogenchloride; thionyl chloride; sodium ethanolate; In acetic acid; benzene;

Reference yield:

4-(4-Hydroxy-7,8-dimethyl-2-oxo-1,2-dihydro-quinolin-3-yl)-2,4-dioxo-butyric acid ethyl ester → repirinast (73080-51-0)

Guidance literature:

Multi-step reaction with 3 steps

1: conc. hydrochloric acid / acetic acid / 0.67 h / 100 °C

2: thionyl chloride / 7 h / Heating

3: 2 h / Heating

With hydrogenchloride; thionyl chloride; In acetic acid;

Reference yield:

2,3-Dimethylaniline (87-59-2) → repirinast (73080-51-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 32 percent / α-chloronaphthalene / 1.5 h / 220 - 235 °C

2: sodium ethylate / benzene / 2 h / Heating

3: conc. hydrochloric acid / acetic acid / 0.67 h / 100 °C

4: thionyl chloride / 7 h / Heating

5: 2 h / Heating

With hydrogenchloride; thionyl chloride; sodium ethanolate; 1-Chloronaphthalene; In acetic acid; benzene;

upstream raw materials:

i-Amyl alcohol

7,8-Dimethyl-4,5-dioxo-5,6-dihydro-4H-pyrano[3,2-c]quinoline-2-carbonyl chloride

3-acetyl-4-hydroxy-7,8-dimethyl-2-quinolone

MY 1250

Refernces