(S)-3-phenyl-N₁-(2-(pyridin-4-yl)-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidin-4-yl)propane-1,2-diamine

Base Information

• Chemical Name: (S)-3-phenyl-N₁-(2-(pyridin-4-yl)-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidin-4-yl)propane-1,2-diamine
• CAS No.: 1438881-19-6
• Molecular Formula: C₂₄H₂₅N₅S
• Molecular Weight: 415.562

Synonyms:(S)-3-phenyl-N₁-(2-(pyridin-4-yl)-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidin-4-yl)propane-1,2-diamine

Chemical Property of (S)-3-phenyl-N₁-(2-(pyridin-4-yl)-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidin-4-yl)propane-1,2-diamine

Chemical Property:

Purity/Quality:

97% ^*data from raw suppliers

(2S)-3-Phenyl-N1-[5,6,7,8-tetrahydro-2-(4-pyridinyl)[1]benzothieno[2,3-d]pyrimidin-4-yl]-1,2-propanediamine ^*data from reagent suppliers

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Useful:

• Description: CRT0066854 is an inhibitor of PKCι and PKCζ (IC50s = 132 and 639 nM, respectively). It also inhibits the Rho-associated kinase II (ROCK2) kinase domain (IC50 = 620 nM). It is selective for these atypical PKCs and ROCK2 over typical PKCs and 98 other kinases in a panel at 1 μM. CRT0066854 decreases phosphorylation of the atypical PKC substrate lethal giant larvae 2 (LLGL2) in HEK293 cells expressing PKCι and LLGL2. It decreases viability of A549 lung carcinoma cells (IC50 = 3.47 μM) and decreases colony formation in HeLa cells by 65% when used at a concentration of 1 μM. CRT0066854 impairs lumen formation in MDCK cells in a Matrigel? assay and migration of NRK-49F cells in a wound assay.
• Uses: (2S)-3-Phenyl-N1-[5,6,7,8-tetrahydro-2-(4-pyridinyl)[1]benzothieno[2,3-d]pyrimidin-4-yl]-1,2-propanediamine, is used in the synthesis of synthesis of Alpha protein kinase C (PKC) inhibitor.

Technology Process of (S)-3-phenyl-N₁-(2-(pyridin-4-yl)-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidin-4-yl)propane-1,2-diamine

There total 5 articles about (S)-3-phenyl-N₁-(2-(pyridin-4-yl)-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidin-4-yl)propane-1,2-diamine 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:

2,4,6-triisopropylbenzenesulfonic acid 2-pyridin-4-yl-5,6,7,8-tetrahydro-benzo[4,5]thieno[2,3-d]pyrimidin-4-yl ester (1438887-05-8) + (2S)-3-phenylpropane-1,2-diamine (85612-60-8) → (S)-3-phenyl-N1-(2-(pyridin-4-yl)-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidin-4-yl)propane-1,2-diamine (1438881-19-6)

Guidance literature:

With triethylamine; In N,N-dimethyl acetamide; at 20 ℃; for 2h;

DOI:10.1042/BJ20121871

Reference yield:

pyridine-4-carbonitrile (100-48-1) → (S)-3-phenyl-N1-(2-(pyridin-4-yl)-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidin-4-yl)propane-1,2-diamine (1438881-19-6)

Guidance literature:

Multi-step reaction with 3 steps

1: potassium 2-methylbutan-2-olate / 1,4-dioxane; toluene / 20 °C

2: triethylamine; dmap / dichloromethane / 1 h / 20 °C

3: triethylamine / N,N-dimethyl acetamide / 2 h / 20 °C

With dmap; potassium 2-methylbutan-2-olate; triethylamine; In 1,4-dioxane; dichloromethane; N,N-dimethyl acetamide; toluene;

DOI:10.1042/BJ20121871

Reference yield:

ethyl 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate (4506-71-2) → (S)-3-phenyl-N1-(2-(pyridin-4-yl)-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidin-4-yl)propane-1,2-diamine (1438881-19-6)

Guidance literature:

Multi-step reaction with 3 steps

1: potassium 2-methylbutan-2-olate / 1,4-dioxane; toluene / 20 °C

2: triethylamine; dmap / dichloromethane / 1 h / 20 °C

3: triethylamine / N,N-dimethyl acetamide / 2 h / 20 °C

With dmap; potassium 2-methylbutan-2-olate; triethylamine; In 1,4-dioxane; dichloromethane; N,N-dimethyl acetamide; toluene;

DOI:10.1042/BJ20121871

upstream raw materials:

pyridine-4-carbonitrile

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

2-pyridin-4-yl-5,6,7,8-tetrahydro-benzo[4,5]thieno[2,3-d]pyrimidin-4-ol

2,4,6-triisopropylbenzenesulfonic acid 2-pyridin-4-yl-5,6,7,8-tetrahydro-benzo[4,5]thieno[2,3-d]pyrimidin-4-yl ester

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