6-methyl-2-sulfanyl-7,8-dihydro-5H-1,6-naphthyridine-3-carbonitrile

Base Information

• Chemical Name: 6-methyl-2-sulfanyl-7,8-dihydro-5H-1,6-naphthyridine-3-carbonitrile
• CAS No.: 290299-52-4
• Molecular Formula: C₁₀H₁₁N₃S
• Molecular Weight: 205.283
• DSSTox Substance ID: DTXSID701149472

Synonyms:SCHEMBL14954856;WKHDSLWYTOIAGN-UHFFFAOYSA-N;DTXSID701149472;6-methyl-2-sulfanyl-7,8-dihydro-5H-1,6-naphthyridine-3-carbonitrile;AKOS003578523;AKOS003593814;290299-52-4;1,2,5,6,7,8-Hexahydro-6-methyl-2-thioxo-1,6-naphthyridine-3-carbonitrile;3-cyano-6-methyl-5,6,7,8-tetrahydro-1,6-naphthyridine-2(1h)-thione

Chemical Property of 6-methyl-2-sulfanyl-7,8-dihydro-5H-1,6-naphthyridine-3-carbonitrile

Chemical Property:

• XLogP3: 0.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 205.06736854
• Heavy Atom Count: 14
• Complexity: 397

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CN1CCC2=C(C1)C=C(C(=S)N2)C#N

Technology Process of 6-methyl-2-sulfanyl-7,8-dihydro-5H-1,6-naphthyridine-3-carbonitrile

There total 4 articles about 6-methyl-2-sulfanyl-7,8-dihydro-5H-1,6-naphthyridine-3-carbonitrile 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: 54.0%

Cyanothioacetamide (7357-70-2) + 1-methyl-3-(2-piperidinomethylene)-4-piperidone → 6-methyl-1,2,5,6,7,8-hexahydro-2-thioxo-1,6-naphthyridine-3-carbonitrile (290299-52-4)

Guidance literature:

With hydrogen cation;

DOI:10.1007/BF02269560

Reference yield: 52.0%

Cyanothioacetamide (7357-70-2) + sodium 1-methyl-4-oxopiperidine-3-carbaldehyde enolate → 6-methyl-1,2,5,6,7,8-hexahydro-2-thioxo-1,6-naphthyridine-3-carbonitrile (290299-52-4)

Guidance literature:

Cyanothioacetamide; sodium 1-methyl-4-oxopiperidine-3-carbaldehyde enolate; With piperdinium acetate; In water; for 24h; Inert atmosphere; Reflux;

With acetic acid; In water; at 20 ℃; Inert atmosphere;

DOI:10.1016/j.bmc.2021.116092

Reference yield:

1-Methyl-4-piperidone (1445-73-4) + Cyanothioacetamide (7357-70-2) + formic acid ethyl ester (109-94-4) → 6-methyl-1,2,5,6,7,8-hexahydro-2-thioxo-1,6-naphthyridine-3-carbonitrile (290299-52-4)

Guidance literature:

1-Methyl-4-piperidone; formic acid ethyl ester; With sodium; In diethyl ether;

Cyanothioacetamide; In ethanol;

DOI:10.3184/030823408X296366

upstream raw materials:

Cyanothioacetamide

1-Methyl-4-piperidone

formic acid ethyl ester

formaldehyd

Downstream raw materials:

6-amino-5-cyano-2-(3-cyano-6-methyl-5,6,7,8-tetrahydro-[1,6]naphthyridin-2-ylsulfanylmethyl)-4-(2-fluoro-phenyl)-4H-pyran-3-carboxylic acid methyl ester

6-amino-5-cyano-2-(3-cyano-6-methyl-5,6,7,8-tetrahydro-[1,6]naphthyridin-2-ylsulfanylmethyl)-4-(2-trifluoromethyl-phenyl)-4H-pyran-3-carboxylic acid ethyl ester

C₂₅H₂₂FN₅O₃S

C₂₀H₂₀N₄O₂S

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