2-(6-(4-(2-Chloro-5-fluorophenoxy)piperidin-1-yl)pyridazin-3-yl)-5-methyl-1,3,4-oxadiazole

Base Information

• Chemical Name: 2-(6-(4-(2-Chloro-5-fluorophenoxy)piperidin-1-yl)pyridazin-3-yl)-5-methyl-1,3,4-oxadiazole
• CAS No.: 944808-88-2
• Molecular Formula: C₁₈H₁₇ClFN₅O₂
• Molecular Weight: 389.817
• ChEMBL ID: CHEMBL226646
• DSSTox Substance ID: DTXSID80587445
• Pharos Ligand ID: 4B9R1ZPJHXVT
• Wikidata: Q82479873
• Mol file: 944808-88-2.mol

Synonyms:2-(6-(4-(2-chloro-5-fluorophenoxy)piperidin-1-yl)pyridazin-3-yl)-5-methyl-1,3,4-oxadiazole;cay-10566;CAY10566;DFP2M-oxadiazole

Chemical Property of 2-(6-(4-(2-Chloro-5-fluorophenoxy)piperidin-1-yl)pyridazin-3-yl)-5-methyl-1,3,4-oxadiazole

Chemical Property:

• Melting Point: 160 - 170°C
• Boiling Point: 600.2±65.0 °C(Predicted)
• PKA: 2.01±0.10(Predicted)
• Density: 1.369±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 4
• Exact Mass: 389.1054807
• Heavy Atom Count: 27
• Complexity: 485

Purity/Quality:

97% ^*data from raw suppliers

CAY10566 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=NN=C(O1)C2=NN=C(C=C2)N3CCC(CC3)OC4=C(C=CC(=C4)F)Cl
• Description: Stearoyl-CoA desaturase (SCD) catalyzes the committed step of the conversion of saturated, long-chain fatty acids to monounsaturated fatty acids. The SCD1 gene is thought to play a key role in lipid homeostasis and body weight regulation. Thus, modulating SCD1 activity pharmacologically may be a useful tool for regulating type 2 diabetes, dyslipidemia, and obesity. CAY10566 is a potent and selective inhibitor of SCD1 that demonstrates IC50 values of 4.5 and 26 nM in mouse and human enzymatic assays, respectively. CAY10566 inhibits the conversion of saturated, long-chain fatty acyl-CoAs to monounsaturated, long-chain fatty acyl-CoAs in HepG2 cells with IC50 values of 7.9 and 6.8 nM, respectively, when heptadecanoic acid and palmitic acid are used as the substrate.
• Uses: CAY10566, is a stearoyl-CoA desaturase (SCD) inhibitor.

Technology Process of 2-(6-(4-(2-Chloro-5-fluorophenoxy)piperidin-1-yl)pyridazin-3-yl)-5-methyl-1,3,4-oxadiazole

There total 6 articles about 2-(6-(4-(2-Chloro-5-fluorophenoxy)piperidin-1-yl)pyridazin-3-yl)-5-methyl-1,3,4-oxadiazole 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: 52.0%

N'-acetyl-6-[4-(2-chloro-5-fluorophenoxy)piperidin-1-yl]pyridazine-3-carbohydrazine (944808-85-9) → (3-[4-(2-chloro-5-fluorophenoxy)-1-piperidinyl]-6-(5-methyl-1,3,4-oxadiazol-2-yl)-pyridazine) (944808-88-2)

Guidance literature:

With trichlorophosphate; at 100 ℃; for 6h;

DOI:10.1021/jm070219p

Reference yield:

3-chloro-6-[4-(2-chloro-5-fluorophenoxy)piperidin-1-yl]pyridazine (944808-82-6) → (3-[4-(2-chloro-5-fluorophenoxy)-1-piperidinyl]-6-(5-methyl-1,3,4-oxadiazol-2-yl)-pyridazine) (944808-88-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 75 percent / [1,1'-bis(diphenylphosphino)ferrocene]PdCl₂(II)*CH₂Cl₂ / 3 h / 100 °C / 10343.2 Torr

2: 95 percent / aq. NaOH / methanol / 3 h / 25 °C

3: 92 percent / O-benzotriazol-1-yl-N,N,N',N'-tetramethyluronium⁽¹⁺⁾*BF₄^(1-); Et₃N / dimethylformamide / 1 h / 25 °C / pH 6

4: 52 percent / POCl₃ / 6 h / 100 °C

With sodium hydroxide; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triethylamine; trichlorophosphate; [1,1'-bis(diphenylphosphino)ferrocene]PdCl₂(II)*CH₂Cl₂; In methanol; N,N-dimethyl-formamide;

DOI:10.1021/jm070219p

Reference yield:

2-chloro-5-fluoro-phenol (3827-49-4) → (3-[4-(2-chloro-5-fluorophenoxy)-1-piperidinyl]-6-(5-methyl-1,3,4-oxadiazol-2-yl)-pyridazine) (944808-88-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 51 percent / triphenylphosphine; di-tert-butyl azodicarboxylate / tetrahydrofuran / 2 h / 25 °C

2: 75 percent / [1,1'-bis(diphenylphosphino)ferrocene]PdCl₂(II)*CH₂Cl₂ / 3 h / 100 °C / 10343.2 Torr

3: 95 percent / aq. NaOH / methanol / 3 h / 25 °C

4: 92 percent / O-benzotriazol-1-yl-N,N,N',N'-tetramethyluronium⁽¹⁺⁾*BF₄^(1-); Et₃N / dimethylformamide / 1 h / 25 °C / pH 6

5: 52 percent / POCl₃ / 6 h / 100 °C

With sodium hydroxide; di-tert-butyl-diazodicarboxylate; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triethylamine; triphenylphosphine; trichlorophosphate; [1,1'-bis(diphenylphosphino)ferrocene]PdCl₂(II)*CH₂Cl₂; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; 1: Mitsunobu reaction;

DOI:10.1021/jm070219p

upstream raw materials:

N'-acetyl-6-[4-(2-chloro-5-fluorophenoxy)piperidin-1-yl]pyridazine-3-carbohydrazine

3-chloro-6-[4-(2-chloro-5-fluorophenoxy)piperidin-1-yl]pyridazine

methyl 6-[4-(2-chloro-5-fluorophenoxy)piperidin-1-yl]pyridazine-3-carboxylate

6-[4-(2-chloro-5-fluorophenoxy)piperidin-1-yl]pyridazine-3-carboxylic acid