Tert-butyl 2-cyano-7,8-dihydro-1,6-naphthyridine-6(5H)-carboxylate

Base Information

• Chemical Name: Tert-butyl 2-cyano-7,8-dihydro-1,6-naphthyridine-6(5H)-carboxylate
• CAS No.: 259809-46-6
• Molecular Formula: C₁₄H₁₇N₃O₂
• Molecular Weight: 259.308
• DSSTox Substance ID: DTXSID10467327
• Wikidata: Q82294248
• Mol file: 259809-46-6.mol

Synonyms:259809-46-6;TERT-BUTYL 2-CYANO-7,8-DIHYDRO-1,6-NAPHTHYRIDINE-6(5H)-CARBOXYLATE;6-Boc-5,6,7,8-tetrahydro-1,6-naphthyridine-2-carbonitrile;Tert-butyl 2-cyano-7,8-dihydro-5H-1,6-naphthyridine-6-carboxylate;MFCD09038017;SCHEMBL3307483;DTXSID10467327;FYOTYCXSXHSVHN-UHFFFAOYSA-N;tert-butyl2-cyano-7,8-dihydro-1,6-naphthyridine-6(5H)-carboxylate;AB49497;SY125412;WS-01749;CS-0047206;FT-0749879;W14939;t-Butyl 2-cyano-7,8-dihydro-1,6-naphthyridine-6(5H)-carboxylate;6-(tert-butoxycarbonyl)-2-cyano-5,6,7,8-tetrahydro-1,6-naphthyridine;tert-butyl 2-cyano-7, 8-dihydro-5H-1, 6-naphthyridine-6-carboxylate;1,6-Naphthyridine-6(5H)-carboxylic acid, 2-cyano-7,8-dihydro-, 1,1-dimethylethyl ester;2-CYANO-7,8-DIHYDRO-5H-[1,6]NAPHTHYRIDINE-6-CARBOXYLIC ACID TERT-BUTYL ESTER

Chemical Property of Tert-butyl 2-cyano-7,8-dihydro-1,6-naphthyridine-6(5H)-carboxylate

Chemical Property:

• Melting Point: 121-124 °C(Solv: dichloromethane (75-09-2); hexane (110-54-3))
• Boiling Point: 401.5±45.0 °C(Predicted)
• PKA: -0.23±0.20(Predicted)
• PSA: 66.22000
• Density: 1.20±0.1 g/cm3(Predicted)
• LogP: 2.18438
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 259.132076794
• Heavy Atom Count: 19
• Complexity: 393

Purity/Quality:

98%min ^*data from raw suppliers

tert-Butyl2-cyano-7,8-dihydro-1,6-naphthyridine-6(5H)-carboxylate 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)C#N

Technology Process of Tert-butyl 2-cyano-7,8-dihydro-1,6-naphthyridine-6(5H)-carboxylate

There total 6 articles about Tert-butyl 2-cyano-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: 88.0%

trimethylsilyl cyanide (7677-24-9) + tert-butyl 1-oxo-7,8-dihydro-5H-1-lambda-5-1,6-naphthyridine-6-carboxylate (259809-45-5) → 6-(tert-butoxycarbonyl)-2-cyano-5,6,7,8-tetrahydro-1,6-naphthyridine (259809-46-6)

Guidance literature:

With N,N-Dimethylcarbamoyl chloride; In dichloromethane; at 20 ℃; for 41h;

DOI:10.1021/jm049884d

Reference yield: 59.0%

N,N-Dimethylcarbamoyl chloride (79-44-7) + tert-butyl 1-oxo-7,8-dihydro-5H-1-lambda-5-1,6-naphthyridine-6-carboxylate (259809-45-5) → 6-(tert-butoxycarbonyl)-2-cyano-5,6,7,8-tetrahydro-1,6-naphthyridine (259809-46-6)

Guidance literature:

6-(tert-butoxycarbonyl)-5,6,7,8-tetrahydro-1,6-naphthyridine-1-oxide; With trimethylsilyl cyanide; In dichloromethane; at 20 ℃; for 0.333333h;

N,N-Dimethylcarbamoyl chloride; In dichloromethane; at 20 ℃; for 41h;

Reference yield:

1-phenylmethyl-4-piperidone (3612-20-2) → 6-(tert-butoxycarbonyl)-2-cyano-5,6,7,8-tetrahydro-1,6-naphthyridine (259809-46-6)

Guidance literature:

Multi-step reaction with 5 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

4: 98 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 0.5 h / 0 °C

5: 88 percent / N,N-dimethylcarbamyl chloride / CH₂Cl₂ / 41 h / 20 °C

With sodium hydroxide; hydrogen; pyridinium acetate; acetic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; N,N-Dimethylcarbamoyl chloride; palladium on activated charcoal; In dichloromethane; toluene;

DOI:10.1021/jm049884d

upstream raw materials:

trimethylsilyl cyanide

tert-butyl 1-oxo-7,8-dihydro-5H-1-lambda-5-1,6-naphthyridine-6-carboxylate

1-phenylmethyl-4-piperidone

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

Downstream raw materials:

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