N-(5-(((5-(1,1-Dimethylethyl)-2-oxazolyl)methyl)thio)-2-thiazolyl)-4-piperidinecarboxamide

Base Information

• Chemical Name: N-(5-(((5-(1,1-Dimethylethyl)-2-oxazolyl)methyl)thio)-2-thiazolyl)-4-piperidinecarboxamide
• CAS No.: 345627-80-7
• Deprecated CAS: 936487-64-8
• Molecular Formula: C17H24N4O2S2
• Molecular Weight: 380.535
• Hs Code.: 29349990
• UNII: 9979I93686
• DSSTox Substance ID: DTXSID50188100
• Nikkaji Number: J1.905.362H
• Wikidata: Q27075347
• NCI Thesaurus Code: C62523
• Pharos Ligand ID: DDPQTBR44PD1
• Metabolomics Workbench ID: 149603
• ChEMBL ID: CHEMBL296468
• Mol file: 345627-80-7.mol

Synonyms:BMS 387032;BMS-387032;BMS387032;N-(5-(((5-(1,1-dimethylethyl)-2-oxazolyl)methyl)thio)-2-thiazolyl)-4-piperidinecarboxamide;SNS 032;SNS-032

Chemical Property of N-(5-(((5-(1,1-Dimethylethyl)-2-oxazolyl)methyl)thio)-2-thiazolyl)-4-piperidinecarboxamide

Chemical Property:

• Melting Point: 171-173 °C
• Refractive Index: 1.606
• PKA: 7.33±0.70(Predicted)
• PSA: 133.59000
• Density: 1.288 g/cm³
• LogP: 4.06080
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 6
• Exact Mass: 380.13406837
• Heavy Atom Count: 25
• Complexity: 454

Purity/Quality:

97% ^*data from raw suppliers

SNS032 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)C1=CN=C(O1)CSC2=CN=C(S2)NC(=O)C3CCNCC3
• Recent ClinicalTrials: Study of Intravenously Administered SNS-032 in Patients With Advanced B-lymphoid Malignancies
• Description: Cyclin-dependent kinases (CDKs) are key regulators of cell cycle progression and are therefore promising targets for cancer therapy. SNS-032 is an ATP-competitive inhibitor of Cdk9, 2, and 7 with IC50 values of 4, 38, and 62 nM, respectively. It is selective for these kinases and displays no additional activity against a panel of 190 kinases (IC50s = >1,000 nM). SNS-032 can block the cell cycle, inhibit transcription, and induce apoptosis in multiple myeloma RPMI-8226 cells with an IC90 value of 0.3 μM. N-[5-[(5-tert-butyl-1,3-oxazol-2-yl)methylsulfanyl]-1,3-thiazol-2-yl]piperidine-4-carboxamide has been shown to induce apoptosis by inhibiting the transcription of the anti-apoptotic proteins, Mcl-1 and XIAP.
• Uses: SNS 032 is a selective inhibitor of Cyclin-dependent Kinase (CDK) 2,7, and 9.

Technology Process of N-(5-(((5-(1,1-Dimethylethyl)-2-oxazolyl)methyl)thio)-2-thiazolyl)-4-piperidinecarboxamide

There total 11 articles about N-(5-(((5-(1,1-Dimethylethyl)-2-oxazolyl)methyl)thio)-2-thiazolyl)-4-piperidinecarboxamide 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: 82.0%

tert-butyl 4-(5-((5-tert-butyloxazol-2-yl)methylthio)thiazol-2-yl-carbamoyl)piperidine-1-carboxylate (345629-23-4) → SNS-032 (345627-80-7)

Guidance literature:

tert-butyl 4-(5-((5-tert-butyloxazol-2-yl)methylthio)thiazol-2-yl-carbamoyl)piperidine-1-carboxylate; With trifluoroacetic acid; In dichloromethane; at 30 ℃; for 3h;

With sodium hydrogencarbonate; In dichloromethane; pH=7 - 8;

Reference yield:

1-azido-3,3-dimethyl-2-butanone (76779-98-1) → SNS-032 (345627-80-7)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 28.0 g / aq. HCl; H₂ / Pd/C / methanol / 2 h / 1034.3 Torr

2.1: 98 percent / Et₃N / CH₂Cl₂ / 1 h / -10 °C

3.1: 80 percent / POCl₃ / 1 h / 105 °C

4.1: NaBH₄ / ethanol / 1 h / 20 °C

4.2: 94 percent / ethanol; acetone / 1 h / Heating

5.1: 76 percent / 4-(dimethylamino)pyridine; 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; Et₃N / dimethylformamide; CH₂Cl₂ / 1.5 h / 20 °C

6.1: 13.3 g / HCl / CHCl₃; dioxane / 14 h / 45 - 60 °C

With hydrogenchloride; dmap; sodium tetrahydroborate; hydrogen; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; trichlorophosphate; palladium on activated charcoal; In 1,4-dioxane; methanol; ethanol; dichloromethane; chloroform; N,N-dimethyl-formamide;

DOI:10.1021/jm0305568

Reference yield:

1-Bromopinacolon (5469-26-1) → SNS-032 (345627-80-7)

Guidance literature:

Multi-step reaction with 7 steps

1.1: NaN₃ / acetone / 20 °C

2.1: 28.0 g / aq. HCl; H₂ / Pd/C / methanol / 2 h / 1034.3 Torr

3.1: 98 percent / Et₃N / CH₂Cl₂ / 1 h / -10 °C

4.1: 80 percent / POCl₃ / 1 h / 105 °C

5.1: NaBH₄ / ethanol / 1 h / 20 °C

5.2: 94 percent / ethanol; acetone / 1 h / Heating

6.1: 76 percent / 4-(dimethylamino)pyridine; 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; Et₃N / dimethylformamide; CH₂Cl₂ / 1.5 h / 20 °C

7.1: 13.3 g / HCl / CHCl₃; dioxane / 14 h / 45 - 60 °C

With hydrogenchloride; dmap; sodium tetrahydroborate; sodium azide; hydrogen; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; trichlorophosphate; palladium on activated charcoal; In 1,4-dioxane; methanol; ethanol; dichloromethane; chloroform; N,N-dimethyl-formamide; acetone;

DOI:10.1021/jm0305568

upstream raw materials:

tert-butyl 4-(5-((5-tert-butyloxazol-2-yl)methylthio)thiazol-2-yl-carbamoyl)piperidine-1-carboxylate

isonipecotic acid

1-azido-3,3-dimethyl-2-butanone

1-Bromopinacolon