2-chloro-N-[4-(4-methoxyphenyl)-1,3-thiazol-2-yl]-N-(3-methoxypropyl)acetamide

Base Information

• Chemical Name: 2-chloro-N-[4-(4-methoxyphenyl)-1,3-thiazol-2-yl]-N-(3-methoxypropyl)acetamide
• CAS No.: 917562-33-5
• Molecular Formula: C₁₆H₁₉ClN₂O₃S
• Molecular Weight: 354.857
• ChEMBL ID: CHEMBL4516422
• DSSTox Substance ID: DTXSID401336571
• Nikkaji Number: J3.537.148F
• Pharos Ligand ID: H9JW6VNCQ7UQ
• Wikipedia: JT-010
• Mol file: 917562-33-5.mol

Synonyms:2-chloro-N-(4-(4-methoxyphenyl)thiazol-2-yl)-N-(3-methoxypropyl)-acetamide;JT010

Chemical Property of 2-chloro-N-[4-(4-methoxyphenyl)-1,3-thiazol-2-yl]-N-(3-methoxypropyl)acetamide

Chemical Property:

• XLogP3: 3.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 8
• Exact Mass: 354.0804913
• Heavy Atom Count: 23
• Complexity: 367

Purity/Quality:

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

JT010 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: COCCCN(C1=NC(=CS1)C2=CC=C(C=C2)OC)C(=O)CCl
• Description: JT010 is a transient receptor potential ankyrin 1 (TRPA1) agonist (EC50 = 0.65 nM in a calcium influx assay). It is selective for TRPA1 over TRP vanilloid 1 (TRPV1), TRPV3, TRPV4, TRP canonical channel 5 (TRPC5), TRP melastatin 2 (TRPM2), and TRPM8 channels at 1 μM.
• Uses: JT010 is a potent and selective TRPA1 channel activator (EC50 = 65 nM); activates the TRPA1 channel by covalently and site-selectively binding to Cys621. Exhibits selectivity for TRPA1 over TRPV1, TRPV3, TRPV4, TRPM2, TRPM8, and TRPC5 channels (EC50 values are >1 μM).

Technology Process of 2-chloro-N-[4-(4-methoxyphenyl)-1,3-thiazol-2-yl]-N-(3-methoxypropyl)acetamide

There total 4 articles about 2-chloro-N-[4-(4-methoxyphenyl)-1,3-thiazol-2-yl]-N-(3-methoxypropyl)acetamide 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: 43.0%

4-(4-methoxyphenyl)-N-(3-methoxypropyl)thiazol-2-amine + chloroacetyl chloride (79-04-9) → JT010 (917562-33-5)

Guidance literature:

With triethylamine; In ethyl acetate; at 0 ℃; for 4.5h;

DOI:10.1021/jacs.5b10162

Reference yield:

3-methoxy-N-(4-(4-methoxyphenyl)thiazol-2-yl)propanamide → JT010 (917562-33-5)

Guidance literature:

Multi-step reaction with 2 steps

1: lithium aluminium tetrahydride / tetrahydrofuran / 6.5 h / 0 °C / Inert atmosphere

2: triethylamine / ethyl acetate / 4.5 h / 0 °C

With lithium aluminium tetrahydride; triethylamine; In tetrahydrofuran; ethyl acetate;

DOI:10.1021/jacs.5b10162

Reference yield:

2-Bromo-4'-methoxyacetophenone (2632-13-5) → JT010 (917562-33-5)

Guidance literature:

Multi-step reaction with 4 steps

1: ethanol / 2 h / Reflux

2: N-ethyl-N,N-diisopropylamine; 6-chloro-3-((dimethylamino)(dimethyliminio)methyl)-1H-benzo[d][1,2,3]triazol-3-ium-1-olatehexafluorophosphate(V) / N,N-dimethyl-formamide / 96 h / 20 °C

3: lithium aluminium tetrahydride / tetrahydrofuran / 6.5 h / 0 °C / Inert atmosphere

4: triethylamine / ethyl acetate / 4.5 h / 0 °C

With lithium aluminium tetrahydride; 6-chloro-3-((dimethylamino)(dimethyliminio)methyl)-1H-benzo[d][1,2,3]triazol-3-ium-1-olatehexafluorophosphate(V); triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; ethanol; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/jacs.5b10162

upstream raw materials:

chloroacetyl chloride

2-Bromo-4'-methoxyacetophenone

4-(4-methoxyphenyl)-1,3-thiazol-2-amine