5-(3-(ethylsulfonyl)phenyl)-3,8-dimethyl-N-(1-methylpiperidin-4-yl)-9H-pyrido[2,3-b]indole-7-carboxamide

Base Information

• Chemical Name: 5-(3-(ethylsulfonyl)phenyl)-3,8-dimethyl-N-(1-methylpiperidin-4-yl)-9H-pyrido[2,3-b]indole-7-carboxamide
• CAS No.: 934541-31-8
• Molecular Formula: C₂₈H₃₂N₄O₃S
• Molecular Weight: 504.653
• UNII: DM9UIR23R7
• ChEMBL ID: CHEMBL3544932
• DSSTox Substance ID: DTXSID70583097
• Metabolomics Workbench ID: 153685
• NCI Thesaurus Code: C82674
• Nikkaji Number: J3.408.634F
• Pharos Ligand ID: 41TSVPX15U1P
• Wikidata: Q27276478
• Mol file: 934541-31-8.mol

Synonyms:TAK-901

Chemical Property of 5-(3-(ethylsulfonyl)phenyl)-3,8-dimethyl-N-(1-methylpiperidin-4-yl)-9H-pyrido[2,3-b]indole-7-carboxamide

Chemical Property:

• Boiling Point: 761.708 °C at 760 mmHg
• Flash Point: 414.467 °C
• PSA: 103.54000
• Density: 1.335 g/cm³
• LogP: 6.02710
• Solubility.: ≥25.25 mg/mL in DMSO; insoluble in H2O; insoluble in EtOH
• XLogP3: 4.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 504.21951207
• Heavy Atom Count: 36
• Complexity: 884

Purity/Quality:

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

TAK-901 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCS(=O)(=O)C1=CC=CC(=C1)C2=CC(=C(C3=C2C4=C(N3)N=CC(=C4)C)C)C(=O)NC5CCN(CC5)C
• Recent ClinicalTrials: A Phase 1 Dose Escalation Study of TAK-901 in Subjects With Advanced Hematologic Malignancies
• Uses: A novel Aurora B kinase inhibitor with potential antineoplastic activity. It binds to and inhibits the activity of Aurora B, which may result in a decrease in the proliferation of tumor cells that overexpress Aurora B. Aurora B is a positive regulator of mitosis that functions in the attachment of the mitotic spindle to the centromere; the segregation of sister chromatids to each daughter cell; and the separation of daughter cells during cytokinesis. A novel Aurora B kinase inhibitor with potential antineoplastic activity. It binds to and inhibits the activity of Aurora B, which may result in a decrease in the proliferation of tumor cells that overexpress Aurora B. Aurora B is a positive regulator of mitosis that functions in the attachment of the mitotic spindle to the centromere; the segregation of sister chromatids to each daughter cell; and the separation of daughter cells during cytokinesis. It is a COVID19-related research product.

Technology Process of 5-(3-(ethylsulfonyl)phenyl)-3,8-dimethyl-N-(1-methylpiperidin-4-yl)-9H-pyrido[2,3-b]indole-7-carboxamide

There total 9 articles about 5-(3-(ethylsulfonyl)phenyl)-3,8-dimethyl-N-(1-methylpiperidin-4-yl)-9H-pyrido[2,3-b]indole-7-carboxamide 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: 94.3%

5-(3-(ethylsulfonyl)phenyl)-3,8-dimethyl-N-(1-methylpiperidin-4-yl)-9H-pyrido[2,3-b]indole-7-carboxamide monohydrochloride (934542-50-4) → 5-(3-(ethylsulfonyl)phenyl)-3,8-dimethyl-N-(1-methylpiperidin-4-yl)-9H-pyrido[2,3-b]indole-7-carboxamide (934541-31-8)

Guidance literature:

With sodium hydrogencarbonate; In water; acetonitrile; at 20 ℃; for 0.25h;

Reference yield: 81.8%

4-Amino-1-methylpiperidine (41838-46-4) + 5-[3-(ethylsulfonyl)phenyl]-3,8-dimethyl-9H-pyrido[2,3-b]indole-7-carboxylic acid (934542-76-4) → 5-(3-(ethylsulfonyl)phenyl)-3,8-dimethyl-N-(1-methylpiperidin-4-yl)-9H-pyrido[2,3-b]indole-7-carboxamide (934541-31-8)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; HATU; In dichloromethane; N,N-dimethyl-formamide; at 20 ℃; for 0.5h;

Reference yield:

2,3-dichloro-5-trifluoromethyl-6-methylnitrobenzene (115571-66-9) → 5-(3-(ethylsulfonyl)phenyl)-3,8-dimethyl-N-(1-methylpiperidin-4-yl)-9H-pyrido[2,3-b]indole-7-carboxamide (934541-31-8)

Guidance literature:

Multi-step reaction with 6 steps

1: copper / 1-methyl-pyrrolidin-2-one / 2 h / 190 °C

2: caesium carbonate / bis(dibenzylideneacetone)-palladium⁽⁰⁾; tricyclohexylphosphine / 1,4-dioxane / 4.5 h / Reflux

3: iron; acetic acid / water / 2 h / 80 °C

4: 3 h / Reflux

5: sulfuric acid / 0.5 h / 120 °C

6: diethylamine; HATU / dichloromethane; N,N-dimethyl-formamide / 0.5 h / 20 °C

With sulfuric acid; iron; copper; caesium carbonate; acetic acid; diethylamine; HATU; bis(dibenzylideneacetone)-palladium⁽⁰⁾; tricyclohexylphosphine; In 1,4-dioxane; 1-methyl-pyrrolidin-2-one; dichloromethane; water; N,N-dimethyl-formamide;

upstream raw materials:

4-Amino-1-methylpiperidine

5-[3-(ethylsulfonyl)phenyl]-3,8-dimethyl-9H-pyrido[2,3-b]indole-7-carboxylic acid

5-(3-(ethylsulfonyl)phenyl)-3,8-dimethyl-N-(1-methylpiperidin-4-yl)-9H-pyrido[2,3-b]indole-7-carboxamide monohydrochloride

2,3-dichloro-5-trifluoromethyl-6-methylnitrobenzene

Refernces

• 1、 -. "POLYMORPHS OF 5-(3-(ETHYLSULFONYL)PHENYL)-3,8-DIMETHYL-N-(1-METHYLPIPERIDIN-4-YL)-9H-PYRIDO[2,3-B]INDOLE-7-CARBOXAMIDE AND METHODS OF USE THEREFOR". Page/Page column 48; 50. . Retrieved 2009/12/02.
• 2、 -. "KINASE INHIBITORS". Page/Page column 190. . Retrieved 2010/11/27.