5-(5-methyl-1-(3-(4-(methylsulfonyl)piperidin-1-yl)benzyl)-1H-1,2,4-triazol-3-yl)-3-(4-(trifluoromethoxy)phenyl)-1,2,4-oxadiazole

Product Name: 5-(5-methyl-1-(3-(4-(methylsulfonyl)piperidin-1-yl)benzyl)-1H-1,2,4-triazol-3-yl)-3-(4-(trifluoromethoxy)phenyl)-1,2,4-oxadiazole
CAS No.: 1570496-34-2
Chemical Name: 5-(5-methyl-1-(3-(4-(methylsulfonyl)piperidin-1-yl)benzyl)-1H-1,2,4-triazol-3-yl)-3-(4-(trifluoromethoxy)phenyl)-1,2,4-oxadiazole
Synonyms: CPD1805;CS-2899;IACS-10759;IACS-010759 (IACS010759);IACS-10759 (IACS-010759 );IACS-010759 (IACS-10759 );IACS-010759, 10 mM in DMSO;IACS-010759; IACS 010759; IACS010759; IACS-10759; IACS 10759; IACS10759;5-(5-methyl-1-(3-(4-(methylsulfonyl)piperidin-1-yl)benzyl)-1H-1,2,4-triazol-3-yl)-3-(4-(trifluoromethoxy)phenyl)-1,2,4-ox;5-(5-methyl-1-(3-(4-(methylsulfonyl)piperidin-1-yl)benzyl)-1H-1,2,4-triazol-3-yl)-3-(4-(trifluoromethoxy)phenyl)-1,2,4-oxadiazole
CBNumber: CB43147164
Molecular Formula: C25H25F3N6O4S
Formula Weight: 562.56
MOL File: 1570496-34-2.mol

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5-(5-methyl-1-(3-(4-(methylsulfonyl)piperidin-1-yl)benzyl)-1H-1,2,4-triazol-3-yl)-3-(4-(trifluoromethoxy)phenyl)-1,2,4-oxadiazole Property

Boiling point:: 768.0±70.0 °C(Predicted)
Density: 1.48±0.1 g/cm3(Predicted)
storage temp.: Store at -20°C
solubility: DMSO:24.23(Max Conc. mg/mL);43.07(Max Conc. mM)
DMF:0.1(Max Conc. mg/mL);0.18(Max Conc. mM)
form: A crystalline solid
pka: 3.24±0.40(Predicted)
color: White to off-white
InChIKey: HWJWNWZJUYCGKV-UHFFFAOYSA-N
SMILES: N1(C2=CC=CC(CN3C(C)=NC(C4ON=C(C5=CC=C(OC(F)(F)F)C=C5)N=4)=N3)=C2)CCC(S(C)(=O)=O)CC1

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Cayman Chemical

Product number: 25867
Product name: IACS-010759
Packaging: 1mg
Price: $27
Updated: 2024/03/01

Cayman Chemical

Product number: 25867
Product name: IACS-010759
Packaging: 25mg
Price: $236
Updated: 2024/03/01

Cayman Chemical

Product number: 25867
Product name: IACS-010759
Packaging: 5mg
Price: $88
Updated: 2024/03/01

Cayman Chemical

Product number: 25867
Product name: IACS-010759
Packaging: 10mg
Price: $149
Updated: 2024/03/01

TRC

Product number: M329473
Product name: 4-(Methylsulfonyl)-1-[3-[[5-methyl-3-[3-[4-(trifluoromethoxy)phenyl]-1,2,4-oxadiazol-5-yl]-1H-1,2,4-triazol-1-yl]methyl]phenyl]piperidine(IACS-010759)
Packaging: 25mg
Price: $1175
Updated: 2021/12/16

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5-(5-methyl-1-(3-(4-(methylsulfonyl)piperidin-1-yl)benzyl)-1H-1,2,4-triazol-3-yl)-3-(4-(trifluoromethoxy)phenyl)-1,2,4-oxadiazole Chemical Properties,Usage,Production

Uses

4-(Methylsulfonyl)-1-[3-[[5-methyl-3-[3-[4-(trifluoromethoxy)phenyl]-1,2,4-oxadiazol-5-yl]-1H-1,2,4-triazol-1-yl]methyl]phenyl]piperidine is a drug candidate that acts as a modulator of HIF activity for treatment of cancer and other hypoxia-mediated diseases.

Synthesis

1570494-48-2

290328-55-1

1570496-34-2

2-Dicyclohexylphosphino-2',6'-diisopropoxy-1,1'-biphenyl (580 mg, 1.25 mmol) and tris(dibenzylideneacetone)dipalladium (760 mg, 0.83 mmol) were added to 5-(1-(3-bromobenzyl)-5-methyl-1H-1,2,4-triazol-3-yl)-3-(4-(trifluoromethoxy)phenyl)-1,2 ,4-oxadiazole (2.00 g, 4.16 mmol), 4-methanesulfonylpiperidine (1.02 g, 6.24 mmol) and sodium tert-butanolate (800 mg, 8.33 mmol) in a solution of toluene (80 mL). The reaction mixture was degassed with argon for 3 minutes and then heated to 140 °C under argon atmosphere and kept for 18 hours. Upon completion of the reaction, the mixture was cooled to room temperature, diluted with ethyl acetate (100 mL), filtered through a pad of diatomaceous earth and washed with ethyl acetate (100 mL). The filtrate was concentrated under reduced pressure and the residue was purified by silica gel column chromatography (petroleum ether: ethyl acetate = 1:1 followed by pure ethyl acetate) to give the crude product. The crude product was treated with ethyl acetate and ether (1:9, 30 mL, v/v), and the resulting suspension was stirred at room temperature for 30 min and filtered to afford 5-(5-methyl-1-(3-(4-(methylsulfonyl)piperidin-1-yl)benzyl)-1H-1 ,2,4-triazol-3- yl)-3-(4-(trifluoromethoxy)phenyl)-1 ,2,4-oxadiazole as a white solid (905 mg, 39% yield). The product was characterized by 1H NMR, 13C NMR, 19F NMR and HRMS.

in vivo

IACS-010759 (5, 10, 25 mg/kg/day; oral; for 21 d) results in tumor regression with minimal body weight loss at the 5 or 10 mg/kg dose in mice bearing NB-1 (PGD-null) subcutaneous xenografts. IACS-010759 at the 25 mg/kg dose is not tolerated^[1].
IACS-010759 HCl (10 mg/kg; orally; QD (daily) or QD×5 (5 d on/2 d off); for 35 d) increases median survival from 28 d to longer than 60 d, whereas less-frequent dosing schedules (Q2D or Q3D) enhances survival to a lesser extent^[1].
IACS-010759 (0.3 mg/kg for iv; 1 mg/kg for oral) has low plasma clearance with a high volume of distribution, resulting in a prolonged terminal half-life (>24 h)^[1].

References

[1] Nature Medicine, 2018, vol. 24, # 7, p. 1036 - 1046
[2] Patent: WO2014/31936, 2014, A2. Location in patent: Paragraph 0355
[3] Patent: US2015/239876, 2015, A1. Location in patent: Paragraph 0236; 0240

5-(5-methyl-1-(3-(4-(methylsulfonyl)piperidin-1-yl)benzyl)-1H-1,2,4-triazol-3-yl)-3-(4-(trifluoromethoxy)phenyl)-1,2,4-oxadiazole Preparation Products And Raw materials

Raw materials

Preparation Products

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5-(5-methyl-1-(3-(4-(methylsulfonyl)piperidin-1-yl)benzyl)-1H-1,2,4-triazol-3-yl)-3-(4-(trifluoromethoxy)phenyl)-1,2,4-oxadiazole Suppliers

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1570496-34-2, 5-(5-methyl-1-(3-(4-(methylsulfonyl)piperidin-1-yl)benzyl)-1H-1,2,4-triazol-3-yl)-3-(4-(trifluoromethoxy)phenyl)-1,2,4-oxadiazoleRelated Search:

5-(5-methyl-1-(3-(4-(methylsulfonyl)piperidin-1-yl)benzyl)-1H-1,2,4-triazol-3-yl)-3-(4-(trifluoromethoxy)phenyl)-1,2,4-oxadiazole

IACS-010759 (IACS-10759 )

IACS-10759 (IACS-010759 )

IACS-10759

CS-2899

CPD1805

IACS-010759; IACS 010759; IACS010759; IACS-10759; IACS 10759; IACS10759

5-[5-Methyl-1-[[3-(4-methylsulfonylpiperidin-1-yl)phenyl]methyl]-1,2,4-triazol-3-yl]-3-[4-(trifluoromethoxy)phenyl]-1,2,4-oxadiazole

Piperidine, 4-(methylsulfonyl)-1-[3-[[5-methyl-3-[3-[4-(trifluoromethoxy)phenyl]-1,2,4-oxadiazol-5-yl]-1H-1,2,4-triazol-1-yl]methyl]phenyl]-

5-(5-methyl-1-(3-(4-(methylsulfonyl)piperidin-1-yl)benzyl)-1H-1,2,4-triazol-3-yl)-3-(4-(trifluoromethoxy)phenyl)-1,2,4-ox

4-(Methylsulfonyl)-1-[3-[[5-methyl-3-[3-[4-(trifluoromethoxy)phenyl]-1,2,4-oxadiazol-5-yl]-1H-1,2,4-triazol-1-yl]methyl]phenyl]piperidine (IACS-010759)

OXPHOS,phosphorylation,complex,Apoptosis,mitochondrial,IACS-010759,IACS 010759,Inhibitor,orally,inhibit,H460,Mitochondrial Metabolism,AML,oxidative,IACS010759

IACS-010759, 10 mM in DMSO

IACS-010759 (IACS010759)

1570496-34-2

C25H25F3N6O4S

API