Benzonitrile, 5-[3-[(1S)-2,3-dihydro-1-[(2-hydroxyethyl)aMino]-1H-inden-4-yl]-1,2,4-oxadiazol-5-yl]-2-(1-Methylethoxy)- (free base)

Base Information

• Chemical Name: Benzonitrile, 5-[3-[(1S)-2,3-dihydro-1-[(2-hydroxyethyl)aMino]-1H-inden-4-yl]-1,2,4-oxadiazol-5-yl]-2-(1-Methylethoxy)- (free base)
• CAS No.: 1306760-87-1
• Molecular Formula: C₂₃H₂₄N₄O₃
• Molecular Weight: 404.469
• Mol file: 1306760-87-1.mol

Synonyms:Benzonitrile, 5-[3-[(1S)-2,3-dihydro-1-[(2-hydroxyethyl)aMino]-1H-inden-4-yl]-1,2,4-oxadiazol-5-yl]-2-(1-Methylethoxy)- (free base);Ozanimod (RPC1063);Ozanimod;RPC1063;Benzonitrile, 5-[3-[(1S)-2,3-dihydro-1-[(2-hydroxyethyl)amino]-1H-inden-4-yl]-1,2,4-oxadiazol-5-yl]-2-(1-methylethoxy)-;5-[3-[(1S)-2,3-Dihydro-1-[(2-hydroxyethyl)amino]-1H-inden-4-yl]-1,2,4-oxadiazol-5-yl]-2-(1-methylethoxy)benzonitrile;(S)-5-(3-(1-((2-hydroxyethyl)amino)-2,3-dihydro-1H-inden-4-yl)-1,2,4-oxadiazol-5-yl)-2-isopropoxybenzonitrile;oxanimod(RPC1063)

Chemical Property of Benzonitrile, 5-[3-[(1S)-2,3-dihydro-1-[(2-hydroxyethyl)aMino]-1H-inden-4-yl]-1,2,4-oxadiazol-5-yl]-2-(1-Methylethoxy)- (free base)

Chemical Property:

• Boiling Point: 648.3±65.0 °C(Predicted)
• PKA: 14.73±0.10(Predicted)
• PSA: 104.20000
• Density: 1.30±0.1 g/cm3(Predicted)
• LogP: 4.02258
• Storage Temp.: -20°C Freezer
• Solubility.: DMSO (Slightly), Methanol (Slightly)

Purity/Quality:

95%, ^*data from raw suppliers

Ozanimod ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Ozanimod is an agonist that binds to S1P1 and S1P5 receptors. Experiments on rodents revealed that Ozanimod is effective against autoimmune diseases.
• Description: Ozanimod is a sphingosine-1-phosphate receptor 1 (S1P1) and S1P5 agonist. It induces GTPγS binding in cell membranes expressing human S1P1 or S1P5 (EC50s = 0.41 and 11 nM, respectively) but not cell membranes expressing S1P2 or S1P3 receptors (EC50s = >10,000 nM for both). Ozanimod (0.2 mg/kg) reduces the number of peripheral lymphocytes in rats. It reduces disease severity and the number of circulating lymphocytes in a mouse model of experimental autoimmune encephalomyelitis (EAE). Ozanimod (0.3 and 1 mg/kg) reduces disease severity and body weight loss in a mouse model of TNBS-induced colitis. Formulations containing ozanimod have been used in the treatment of relapsing multiple sclerosis and ulcerative colitis.

Technology Process of Benzonitrile, 5-[3-[(1S)-2,3-dihydro-1-[(2-hydroxyethyl)aMino]-1H-inden-4-yl]-1,2,4-oxadiazol-5-yl]-2-(1-Methylethoxy)- (free base)

There total 62 articles about Benzonitrile, 5-[3-[(1S)-2,3-dihydro-1-[(2-hydroxyethyl)aMino]-1H-inden-4-yl]-1,2,4-oxadiazol-5-yl]-2-(1-Methylethoxy)- (free base) 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: 98.36%

5-{3-[(1S)-1-[(2-hydroxyethyl)amino]-2,3-dihydro-1H-inden-4-yl]-1,2,4-oxadiazol-5-yl}-2-(propan-2-yloxy)benzonitrile hydrochloride (1306760-85-9) → 5-(3-{(1S)-1-[(2-hydroxyethyl)amino]-2,3-dihydro-1H-inden-4-yl}-1,2,4-oxadiazol-5-yl)-2-[(propan-2-yl)oxy]benzonitrile (1306760-86-0,1306760-87-1)

Guidance literature:

With sodium hydroxide; In water; pH=Ca.8-9;

Reference yield: 96.0%

5-(3-(1-((2-hydroxyethyl)imino)-2,3-dihydro-1H-inden-4-yl)-1,2,4-oxadiazol-5-yl)-2-isopropoxybenzonitrile → 5-(3-{(1S)-1-[(2-hydroxyethyl)amino]-2,3-dihydro-1H-inden-4-yl}-1,2,4-oxadiazol-5-yl)-2-[(propan-2-yl)oxy]benzonitrile (1306760-86-0,1306760-87-1)

Guidance literature:

With formic acid; C₃-[(S,S)-teth-TrisDPEN RuCl]; ethanolamine; triethylamine; In 2,2,2-trifluoroethanol; at 50 ℃; for 24h; Reagent/catalyst; Solvent; enantioselective reaction; Catalytic behavior;

DOI:10.1002/ejoc.202100058

Reference yield: 90.0%

5-(3-(1-((2-hydroxyethyl)imino)-2,3-dihydro-1H-inden-4-yl)-1,2,4-oxadiazol-5-yl)-2-isopropoxybenzonitrile → 5-(3-(1-((2-hydroxyethyl)amino)-2,3-dihydro-1H-inden-4-yl)-1,2,4-oxadiazol-5-yl)-2-isopropoxybenzonitrile (1201447-13-3,1306760-86-0,1306760-87-1)

Guidance literature:

With sodium tetrahydroborate; ethanol; In dichloromethane; at 0 - 40 ℃; for 1h;

upstream raw materials:

5-(3-(1-hydroxy-2,3-dihydro-1H-inden-4-yl)-1,2,4-oxadiazol-5-yl)-2-isopropoxybenzonitrile

ethanolamine

4-cyano-2,3-dihydro-1H-inden-1-one

(R)-tert-butyl 2-(tert-butyldimethylsilyloxy)ethyl(4-cyano-2,3-dihydro-1H-inden-1-yl)carbamate

Refernces

• 1、 -. "IMPROVED PROCESS FOR PREPARING OZANIMOD". Page/Page column 9-10. . Retrieved 2021/02/12.
• 2、 -. "A PROCESS FOR THE PREPARATION OF OZANIMOD AND ITS INTERMEDIATE (S)-1-AMINO-2,3-DIHYDRO-1H-INDENE-4-CARBONITRILE". . . Retrieved 2020/05/07.