trans-4-[4-[[[5-[(3,4-Difluorophenyl)amino]-1,3,4-oxadiazol-2-yl]carbonyl]amino]phenyl]cyclohexaneacetic acid

Base Information

• Chemical Name: trans-4-[4-[[[5-[(3,4-Difluorophenyl)amino]-1,3,4-oxadiazol-2-yl]carbonyl]amino]phenyl]cyclohexaneacetic acid
• CAS No.: 892489-52-0
• Molecular Formula: C23H22F2N4O4
• Molecular Weight: 456.449
• Mol file: 892489-52-0.mol

Synonyms:(trans-4-;cyclohexa;LogP

Chemical Property of trans-4-[4-[[[5-[(3,4-Difluorophenyl)amino]-1,3,4-oxadiazol-2-yl]carbonyl]amino]phenyl]cyclohexaneacetic acid

Chemical Property:

• Refractive Index: 1.627
• PKA: 4.72±0.10(Predicted)
• PSA: 117.35000
• Density: 1.402 g/cm³
• LogP: 5.23820

Purity/Quality:

95% ^*data from raw suppliers

AZD3988 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: AZD 3988 is a diacylglycerol O-acyltransferase (DGAT) enzyme inhibitor, which has been investigated as potential treatments for diabetes and other metabolic diseases.

Technology Process of trans-4-[4-[[[5-[(3,4-Difluorophenyl)amino]-1,3,4-oxadiazol-2-yl]carbonyl]amino]phenyl]cyclohexaneacetic acid

There total 9 articles about trans-4-[4-[[[5-[(3,4-Difluorophenyl)amino]-1,3,4-oxadiazol-2-yl]carbonyl]amino]phenyl]cyclohexaneacetic acid 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%

methyl (trans-4-{4-[({5-[(3,4-difluorophenyl)amino]-1,3,4-oxadiazol-2-yl}carbonyl)amino]phenyl}cyclohexyl)acetate (892489-51-9) → (trans-4-{4-[({5-[(3,4-difluorophenyl)amino]-1,3,4-oxadiazol-2-yl}carbonyl)amino]phenyl}cyclohexyl)acetic acid (892489-52-0)

Guidance literature:

methyl (trans-4-{4-[({5-[(3,4-difluorophenyl)amino]-1,3,4-oxadiazol-2-yl}carbonyl)amino]phenyl}cyclohexyl)acetate; With methanol; lithium hydroxide; water; at 30 ℃; for 2h;

With hydrogenchloride; In methanol; water; at 0 - 10 ℃; pH=2;

Reference yield:

(trans)-methyl 2-(4-(4-(((trifluoromethyl)sulfonyl)oxy)phenyl)cyclohexyl)acetate (701232-68-0) → (trans-4-{4-[({5-[(3,4-difluorophenyl)amino]-1,3,4-oxadiazol-2-yl}carbonyl)amino]phenyl}cyclohexyl)acetic acid (892489-52-0)

Guidance literature:

Multi-step reaction with 6 steps

1.1: caesium carbonate / palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / tetrahydrofuran / 16 h / Heating / reflux

2.1: hydrogenchloride; methanol; water / 16 h / 4 - 20 °C

2.2: pH 9

3.1: pyridine / dichloromethane / 64 h / 0 - 20 °C

4.1: hydrazine / ethanol; water / 1 h

5.1: N,N-dimethyl acetamide / 2 h / 45 °C

5.2: 3 h / 85 °C

6.1: methanol; lithium hydroxide; water / tetrahydrofuran / 2 h / 30 °C

6.2: 0 - 10 °C / pH 2

With pyridine; hydrogenchloride; methanol; lithium hydroxide; water; caesium carbonate; hydrazine; palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl acetamide; water;

Reference yield:

[4-(4-hydroxyphenyl)cyclohexylidene]acetic acid methyl ester (701232-66-8) → (trans-4-{4-[({5-[(3,4-difluorophenyl)amino]-1,3,4-oxadiazol-2-yl}carbonyl)amino]phenyl}cyclohexyl)acetic acid (892489-52-0)

Guidance literature:

Multi-step reaction with 8 steps

1.1: hydrogen / palladium 10% on activated carbon / tetrahydrofuran / 30 °C / 1500.15 Torr

2.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 17.25 h / 4 - 15 °C

3.1: caesium carbonate / palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / tetrahydrofuran / 16 h / Heating / reflux

4.1: hydrogenchloride; methanol; water / 16 h / 4 - 20 °C

4.2: pH 9

5.1: pyridine / dichloromethane / 64 h / 0 - 20 °C

6.1: hydrazine / ethanol; water / 1 h

7.1: N,N-dimethyl acetamide / 2 h / 45 °C

7.2: 3 h / 85 °C

8.1: methanol; lithium hydroxide; water / tetrahydrofuran / 2 h / 30 °C

8.2: 0 - 10 °C / pH 2

With pyridine; hydrogenchloride; methanol; lithium hydroxide; water; hydrogen; caesium carbonate; N-ethyl-N,N-diisopropylamine; hydrazine; palladium diacetate; palladium 10% on activated carbon; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl acetamide; water;

upstream raw materials:

methyl (trans-4-{4-[({5-[(3,4-difluorophenyl)amino]-1,3,4-oxadiazol-2-yl}carbonyl)amino]phenyl}cyclohexyl)acetate

methyl [trans-4-(4-{[hydrazino(oxo)acetyl]amino}phenyl)cyclohexyl]acetate

[4-(4-hydroxyphenyl)cyclohexylidene]acetic acid methyl ester

trans-[4-(4-aminophenyl)cyclohexyl]acetic acid methyl ester

Refernces