Tert-butyl 7,8-dihydro-1,6-naphthyridine-6(5H)-carboxylate

Base Information

• Chemical Name: Tert-butyl 7,8-dihydro-1,6-naphthyridine-6(5H)-carboxylate
• CAS No.: 259809-44-4
• Molecular Formula: C13H18 N2 O2
• Molecular Weight: 234.29422
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID10467286
• Wikidata: Q72465728
• Mol file: 259809-44-4.mol

Synonyms:259809-44-4;TERT-BUTYL 7,8-DIHYDRO-1,6-NAPHTHYRIDINE-6(5H)-CARBOXYLATE;6-Boc-5,6,7,8-tetrahydro-1,6-naphthyridine;Tert-butyl 7,8-dihydro-5H-1,6-naphthyridine-6-carboxylate;MFCD09038016;7,8-Dihydro-5H-[1,6]naphthyridine-6-carboxylic acid tert-butyl ester;tert-butyl 5,6,7,8-tetrahydro-1,6-naphthyridine-6-carboxylate;1,6-Naphthyridine-6(5H)-carboxylic acid, 7,8-dihydro-, 1,1-dimethylethyl ester;SCHEMBL3263460;DTXSID10467286;BCP08023;AKOS014476120;SB11870;AS-73557;SY277949;CS-0054056;FT-0706106;P10676;A818125;tert-butyl7,8-dihydro-1,6-naphthyridine-6(5H)-carboxylate;tert-butyl 7, 8-dihydro-5H-1, 6-naphthyridine-6-carboxylate

Chemical Property of Tert-butyl 7,8-dihydro-1,6-naphthyridine-6(5H)-carboxylate

Chemical Property:

• Boiling Point: 344℃
• PKA: 5.34±0.20(Predicted)
• Flash Point: 162℃
• PSA: 42.43000
• Density: 1.127
• LogP: 2.31270
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 234.136827821
• Heavy Atom Count: 17
• Complexity: 286

Purity/Quality:

97% ^*data from raw suppliers

6-Boc-5,6,7,8-tetrahydro-1,6-naphthyridine 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N1CCC2=C(C1)C=CC=N2

Technology Process of Tert-butyl 7,8-dihydro-1,6-naphthyridine-6(5H)-carboxylate

There total 8 articles about Tert-butyl 7,8-dihydro-1,6-naphthyridine-6(5H)-carboxylate 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: 64.0%

N-tert-butyloxycarbonylpiperidin-4-one (79099-07-3) + Propargylamine (2450-71-7) → 7,8-dihydro-5H-[1,6]naphthyridine-6-carboxylic acid tert-butyl ester (259809-44-4)

Guidance literature:

With copper(II) choride dihydrate; In isopropyl alcohol; at 60 - 84 ℃; for 12h;

DOI:10.1021/acs.joc.0c03038

Reference yield: 55.0%

di-tert-butyl dicarbonate (24424-99-5) + 5,6,7,8-tetrahydro-1,6-naphthyridine (80957-68-2) → 7,8-dihydro-5H-[1,6]naphthyridine-6-carboxylic acid tert-butyl ester (259809-44-4)

Guidance literature:

With sodium hydroxide; In water; toluene; for 0.333333h;

Reference yield:

1-phenylmethyl-4-piperidone (3612-20-2) → 7,8-dihydro-5H-[1,6]naphthyridine-6-carboxylic acid tert-butyl ester (259809-44-4)

Guidance literature:

Multi-step reaction with 3 steps

1: Et₃N; pyridinium acetate / 22 h / 120 °C

2: H₂; AcOH / Pd/C / 2 h / 50 - 60 °C

3: 981 mg / aq. NaOH / toluene / 0.17 h

With sodium hydroxide; hydrogen; pyridinium acetate; acetic acid; triethylamine; palladium on activated charcoal; In toluene;

DOI:10.1021/jm049884d

upstream raw materials:

di-tert-butyl dicarbonate

5,6,7,8-tetrahydro-1,6-naphthyridine

1-phenylmethyl-4-piperidone

6-benzyl-5,6,7,8-tetrahydro-1,6-naphthyridine

Downstream raw materials:

6-(tert-butoxycarbonyl)-2-cyano-5,6,7,8-tetrahydro-1,6-naphthyridine

6-(tert-butoxycarbonyl)-2-methoxycarbonyl-5,6,7,8-tetrahydro-1,6-naphthyridine

6-(tert-butoxycarbonyl)-5,6,7,8-tetrahydro-1,6-naphthyridine-2-carboxylic acid

tert-butyl octahydro-1,6-naphthyridine-6(2H)carboxylate