2-AMINO-4,5,6,7-TETRAHYDRO-BENZO[B]THIOPHENE-3-CARBOXYLIC ACID BENZYLAMIDE

Base Information

• Chemical Name: 2-AMINO-4,5,6,7-TETRAHYDRO-BENZO[B]THIOPHENE-3-CARBOXYLIC ACID BENZYLAMIDE
• CAS No.: 312513-45-4
• Molecular Formula: C₁₆H₁₈N₂OS
• Molecular Weight: 286.398
• Mol file: 312513-45-4.mol

Synonyms:

Chemical Property of 2-AMINO-4,5,6,7-TETRAHYDRO-BENZO[B]THIOPHENE-3-CARBOXYLIC ACID BENZYLAMIDE

Chemical Property:

• Melting Point: 184-186 °C
• Boiling Point: 483.5±45.0 °C(Predicted)
• PKA: 14.97±0.20(Predicted)
• Density: 1.250±0.06 g/cm3(Predicted)

Purity/Quality:

98%min ^*data from raw suppliers

2-Amino-N-benzyl-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxamide ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi

MSDS Files:

Useful:

Technology Process of 2-AMINO-4,5,6,7-TETRAHYDRO-BENZO[B]THIOPHENE-3-CARBOXYLIC ACID BENZYLAMIDE

There total 5 articles about 2-AMINO-4,5,6,7-TETRAHYDRO-BENZO[B]THIOPHENE-3-CARBOXYLIC ACID BENZYLAMIDE 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: 24.0%

benzylamine (100-46-9) + 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylic acid (5936-58-3) → 2-amino-N-benzyl-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxamide (312513-45-4)

Guidance literature:

With dmap; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 0 - 20 ℃; for 18h;

DOI:10.1039/c6ob00821f

Reference yield:

ethyl 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate (4506-71-2) → 2-amino-N-benzyl-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxamide (312513-45-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 62 percent / KOH / ethanol; H₂O / 5 h / Heating

2: 13 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; 1-hydroxybenzotriazole hydrate; N,N-(dimethylamino)pyridine / CH₂Cl₂ / 16 h / 20 °C

With dmap; potassium hydroxide; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In ethanol; dichloromethane; water;

DOI:10.1016/j.bmc.2005.11.018

Reference yield:

N-Benzylcyanoacetamide (10412-93-8) + cyclohexanone (108-94-1,11119-77-0,9003-41-2,9075-99-4) → 2-amino-N-benzyl-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxamide (312513-45-4)

Guidance literature:

N-Benzylcyanoacetamide; cyclohexanone; With pyridine; titanium tetrachloride; In dichloromethane; at 20 ℃; for 15h; Cooling with ice;

With sulfur; diethylamine; In tetrahydrofuran; at 20 ℃; for 15h;

DOI:10.1002/anie.201411206

upstream raw materials:

benzylamine

2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylic acid

ethyl 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate

N-Benzylcyanoacetamide

Refernces

• 1、 Kuhnert, Maren,K?ster, Helene,Bartholom?us, Ruben,Park, Ah Young,Shahim, Amir,Heine, Andreas,Steuber, Holger,Klebe, Gerhard,Diederich, Wibke E.. "Tracing binding modes in hit-to-lead optimization: Chameleon-like poses of aspartic protease inhibitors". . p. 2849 - 2853. Retrieved 2015/03/04.