Ticolubant

Base Information

• Chemical Name: Ticolubant
• CAS No.: 154413-61-3
• Molecular Formula: C23H19 Cl2 N O3 S
• Molecular Weight: 460.381
• UNII: C1FRU4800P
• Nikkaji Number: J1.100.807K,J771.980I
• Wikidata: Q27275056
• NCI Thesaurus Code: C81669
• Pharos Ligand ID: R1XWWP5RH1HF
• ChEMBL ID: CHEMBL90214
• Mol file: 154413-61-3.mol

Synonyms:3-(6-((2,6-dichlorophenyl)thio)methyl)-3-((2-phenylethoxy)-2-pyridinyl)-2-propenoic acid;SB 209247;SB-209247;Ticolubant

Chemical Property of Ticolubant

Chemical Property:

• Vapor Pressure: 2.67E-16mmHg at 25°C
• Boiling Point: 621.4°Cat760mmHg
• Flash Point: 329.6°C
• PSA: 84.72000
• Density: 1.39g/cm³
• LogP: 6.40000
• XLogP3: 6.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 9
• Exact Mass: 459.0462700
• Heavy Atom Count: 30
• Complexity: 549

Purity/Quality:

95% ^*data from raw suppliers

TICOLUBANT 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)CCOC2=C(N=C(C=C2)CSC3=C(C=CC=C3Cl)Cl)C=CC(=O)O
• Isomeric SMILES: C1=CC=C(C=C1)CCOC2=C(N=C(C=C2)CSC3=C(C=CC=C3Cl)Cl)/C=C/C(=O)O

Technology Process of Ticolubant

There total 8 articles about Ticolubant 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: 60.0%

(E)-3-[6-(2,6-Dichloro-phenylsulfanylmethyl)-3-phenethyloxy-pyridin-2-yl]-acrylic acid methyl ester (170569-20-7) → (E)-3-[6-[[(2,6-dichlorophenyl)-thio]methyl]-3-(2-phenylethoxy)-2-pyridinyl]-2-propenoic acid (154413-61-3)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; methanol; for 18h; Ambient temperature;

DOI:10.1021/jm960248s

Reference yield:

3-hydroxy-6-methylpicolinaldehyde (66497-42-5) → (E)-3-[6-[[(2,6-dichlorophenyl)-thio]methyl]-3-(2-phenylethoxy)-2-pyridinyl]-2-propenoic acid (154413-61-3)

Guidance literature:

Multi-step reaction with 7 steps

1: 85 percent / toluene / 0.5 h / 50 °C

2: 53 percent / Ph₃P, diethyl azodicarboxylate / tetrahydrofuran / 1.25 h / 0 - 20 °C

3: MCPBA / CH₂Cl₂ / 18 h / Ambient temperature

4: trifluoroacetic anhydride / dimethylformamide / 18 h / Ambient temperature

5: SOCl₂ / toluene / 1 h

6: 87 percent / DBU / acetonitrile / 1 h / 50 °C

7: 60 percent / aq. LiOH / methanol; tetrahydrofuran / 18 h / Ambient temperature

With lithium hydroxide; thionyl chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; trifluoroacetic anhydride; diethylazodicarboxylate; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1021/jm960248s

Reference yield:

2-phenylethanol (60-12-8) → (E)-3-[6-[[(2,6-dichlorophenyl)-thio]methyl]-3-(2-phenylethoxy)-2-pyridinyl]-2-propenoic acid (154413-61-3)

Guidance literature:

Multi-step reaction with 6 steps

1: 53 percent / Ph₃P, diethyl azodicarboxylate / tetrahydrofuran / 1.25 h / 0 - 20 °C

2: MCPBA / CH₂Cl₂ / 18 h / Ambient temperature

3: trifluoroacetic anhydride / dimethylformamide / 18 h / Ambient temperature

4: SOCl₂ / toluene / 1 h

5: 87 percent / DBU / acetonitrile / 1 h / 50 °C

6: 60 percent / aq. LiOH / methanol; tetrahydrofuran / 18 h / Ambient temperature

With lithium hydroxide; thionyl chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; trifluoroacetic anhydride; diethylazodicarboxylate; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1021/jm960248s

upstream raw materials:

(E)-3-[6-(2,6-Dichloro-phenylsulfanylmethyl)-3-phenethyloxy-pyridin-2-yl]-acrylic acid methyl ester

3-hydroxy-6-methylpicolinaldehyde

2-phenylethanol

(E)-3-(3-hydroxy-6-methyl-2-pyridinyl)-2-propenoic acid methyl ester

Downstream raw materials:

(E)-N-[N-(tert-Butyloxycarbonyl)-3-aminopropyl]-3-[6-[[(2,6-dichlorophenyl)thio]methyl]-3-(2-phenylethoxy)-2-pyridinyl]-2-propenamide