N-(2-METHYL-6-BENZOOXAZOLYL)-N''-1,5-NAPHTHYRIDIN-4-YL UREA

Base Information

• Chemical Name: N-(2-METHYL-6-BENZOOXAZOLYL)-N''-1,5-NAPHTHYRIDIN-4-YL UREA
• CAS No.: 792173-99-0
• Molecular Formula: C₁₇H₁₃N₅O₂
• Molecular Weight: 319.323
• Mol file: 792173-99-0.mol

Synonyms:N-(2-METHYL-6-BENZOOXAZOLYL)-N’’-1,5-NAPHTHYRIDIN-4-YL UREA

Chemical Property of N-(2-METHYL-6-BENZOOXAZOLYL)-N''-1,5-NAPHTHYRIDIN-4-YL UREA

Chemical Property:

• Vapor Pressure: 2.63E-08mmHg at 25°C
• Refractive Index: 1.793
• Boiling Point: 450.5°C at 760 mmHg
• PKA: 10.21±0.43(Predicted)
• Flash Point: 226.2°C
• PSA: 92.94000
• Density: 1.472
• LogP: 3.86940
• Storage Temp.: room temp
• Solubility.: insoluble in H2O; insoluble in EtOH; ≥14.55 mg/mL in DMSO

Purity/Quality:

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

SB334867 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: SB 334867 is an orexin 1 receptor antagonist.

Technology Process of N-(2-METHYL-6-BENZOOXAZOLYL)-N''-1,5-NAPHTHYRIDIN-4-YL UREA

There total 7 articles about N-(2-METHYL-6-BENZOOXAZOLYL)-N''-1,5-NAPHTHYRIDIN-4-YL UREA 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: 85.0%

4-amino-1,5-naphthyridine (27392-68-3) + 2-methyl-6-benzoxazole carboxylic acid (13452-14-7) → 1-(2-methylbenzoxazol-6-yl)-3-(1,5-naphthyridin-4-yl)urea (792173-99-0)

Guidance literature:

2-methyl-6-benzoxazole carboxylic acid; With diphenyl phosphoryl azide; triethylamine; In toluene; at 20 - 90 ℃; for 1h;

4-amino-1,5-naphthyridine; In N,N-dimethyl-formamide; toluene; at 115 ℃; for 3.5h;

DOI:10.1016/j.bmcl.2012.08.109

Reference yield:

4-hydroxy-1,5-naphthyridine (5423-54-1) → 1-(2-methylbenzoxazol-6-yl)-3-(1,5-naphthyridin-4-yl)urea (792173-99-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 34 percent / 2,6-lutidine

2: 85 percent / n-PrNH₂*HCl

3: (PhO)2P(O)N₃

With 2,6-dimethylpyridine; diphenyl phosphoryl azide; N-propylamine hydrochloride;

DOI:10.1016/S0960-894X(01)00343-2

Reference yield:

methyl 2-methyl-1,3-benzoxazole-6-carboxylate (136663-23-5) → 1-(2-methylbenzoxazol-6-yl)-3-(1,5-naphthyridin-4-yl)urea (792173-99-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: lithium hydroxide monohydrate; water / tetrahydrofuran / 2 h

2.1: diphenyl phosphoryl azide; triethylamine / toluene / 1 h / 20 - 90 °C

2.2: 3.5 h / 115 °C

With lithium hydroxide monohydrate; diphenyl phosphoryl azide; water; triethylamine; In tetrahydrofuran; toluene;

DOI:10.1016/j.bmcl.2012.08.109

upstream raw materials:

4-amino-1,5-naphthyridine

2-methyl-6-benzoxazole carboxylic acid

4-hydroxy-1,5-naphthyridine

trifluoro-methanesulfonic acid [1,5]naphthyridin-4-yl ester

Refernces

• 1、 Porter, Roderick A,Chan, Wai N,Coulton, Steven,Johns, Amanda,Hadley, Michael S,Widdowson, Katherine,Jerman, Jeffrey C,Brough, Stephen J,Coldwell, Martyn,Smart, Darren,Jewitt, Frances,Jeffrey, Phillip,Austin, Nigel. "1,3-Biarylureas as selective non-peptide antagonists of the orexin-1 receptor". . p. 1907 - 1910. Retrieved 2007/10/03.