TERN-101

Base Information

• Chemical Name: TERN-101
• CAS No.: 1103500-20-4
• Molecular Formula: C₂₈H₂₇Cl₂N₃O₄
• Molecular Weight: 540.446
• Mol file: 1103500-20-4.mol

Synonyms:TERN-101

Chemical Property of TERN-101

Chemical Property:

• Boiling Point: 740.1±60.0 °C(Predicted)
• Density: 1.48±0.1 g/cm3(Predicted)

Purity/Quality:

99%+, ^*data from raw suppliers

LY2562175 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Description: LY2562175 is a farnesoid X receptor (FXR) agonist (EC50 = 193 nM in a reporter assay). It is selective for FXR over the glucocorticoid, androgen, mineralocorticoid, and progesterone receptors in HEK293 cells overexpressing the human receptors (EC50s = >10 μM for all in a radioligand binding assay). LY2562175 increases the interaction between FXR and steroid receptor coactivator 1 (SRC-1) with an EC50 value of 121 nM in a cell-free assay. It reduces plasma triglyceride and total cholesterol levels in LDL receptor-null mice (ED50s = 3.4 and 2 mg/kg, respectively). LY2562175 also decreases plasma LDL and increases HDL levels in Zucker diabetic fatty (ZDF) rats when administered at doses of 3, 10, and 30 mg/kg for nine days.
• Uses: LY2562175, is a potent and selective FXR agonist with an EC50 of 193 nM.

Technology Process of TERN-101

There total 13 articles about TERN-101 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: 87.0%

6-{4-[5-cyclopropyl-3-(2,6-dichlorophenyl)isoxazol-4-ylmethoxy]piperidin-1-yl}-1-methyl-1H-indole-3-carboxylic acid methyl ester (1103500-82-8) → TERN-101 (1103500-20-4)

Guidance literature:

6-{4-[5-cyclopropyl-3-(2,6-dichlorophenyl)isoxazol-4-ylmethoxy]piperidin-1-yl}-1-methyl-1H-indole-3-carboxylic acid methyl ester; With lithium hydroxide; In 1,4-dioxane; water; at 80 ℃;

With hydrogenchloride; water; pH=3 - 4; Product distribution / selectivity;

Reference yield: 73.0%

tert-butyl 6-(4-{[3-(2,6-dichlorophenyl)-5-cyclopropylisoxazol-4-yl]methoxy}piperidin-1-yl)-1-methylindole-3-carboxylate (1103500-88-4) → TERN-101 (1103500-20-4)

Guidance literature:

With formic acid; at 20 - 30 ℃; for 24 - 72h; Product distribution / selectivity;

Reference yield:

2,6-dichlorobenzaldoxime (25185-95-9) → TERN-101 (1103500-20-4)

Guidance literature:

Multi-step reaction with 8 steps

1.1: N-chloro-succinimide / N,N-dimethyl-formamide / 1 h / 40 °C / Large scale

2.1: triethylamine / 0.5 h / 20 °C / Large scale

2.2: 10 - 20 °C / Large scale

3.1: diisobutylaluminium hydride / tetrahydrofuran; toluene / 2 h / 0 - 20 °C

4.1: carbon tetrabromide; triphenylphosphine / dichloromethane / 2 h / 0 - 20 °C

5.1: potassium tert-butylate; 18-crown-6 ether / tetrahydrofuran / 0.33 h / 0 - 20 °C

5.2: 14 h / 20 °C

6.1: trifluoroacetic acid / dichloromethane / 1.5 h / 20 °C / Inert atmosphere; Cooling with ice

7.1: copper(l) iodide; L-proline; potassium carbonate / dimethyl sulfoxide / 16 h / 120 °C / Inert atmosphere

8.1: potassium hydroxide / methanol; tetrahydrofuran; 1,4-dioxane / 70 °C / Inert atmosphere

With N-chloro-succinimide; copper(l) iodide; 18-crown-6 ether; carbon tetrabromide; potassium tert-butylate; diisobutylaluminium hydride; potassium carbonate; triethylamine; triphenylphosphine; trifluoroacetic acid; L-proline; potassium hydroxide; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene;

DOI:10.1021/acs.jmedchem.5b01161

upstream raw materials:

6-{4-[5-cyclopropyl-3-(2,6-dichlorophenyl)isoxazol-4-ylmethoxy]piperidin-1-yl}-1-methyl-1H-indole-3-carboxylic acid methyl ester

tert-butyl 6-(4-{[3-(2,6-dichlorophenyl)-5-cyclopropylisoxazol-4-yl]methoxy}piperidin-1-yl)-1-methylindole-3-carboxylate

5-cyclopropyl-3-(2,6-dichlorophenyl)-4-((piperidin-4-yloxy)methyl)isoxazole

2,6-dichlorobenzaldoxime

Refernces

• 1、 -. "COMPOUNDS AND METHODS FOR MODULATING FXR". Page/Page column 46. . Retrieved 2009/03/07.