(3R,3aR,6R,6aR)-6-[[6-chloro-5-(4-phenylphenyl)-1H-imidazo[4,5-b]pyridin-2-yl]oxy]-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3-ol

Base Information

• Chemical Name: (3R,3aR,6R,6aR)-6-[[6-chloro-5-(4-phenylphenyl)-1H-imidazo[4,5-b]pyridin-2-yl]oxy]-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3-ol
• CAS No.: 1394371-71-1
• Molecular Formula: C₂₄H₂₀ClN₃O₄
• Molecular Weight: 449.894
• Mol file: 1394371-71-1.mol

Synonyms:

Chemical Property of (3R,3aR,6R,6aR)-6-[[6-chloro-5-(4-phenylphenyl)-1H-imidazo[4,5-b]pyridin-2-yl]oxy]-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3-ol

Chemical Property:

• Melting Point: 215 - 219oC
• Boiling Point: 716.6±70.0 °C(Predicted)
• Density: 1.437±0.06 g/cm3(Predicted)

Purity/Quality:

99% ^*data from raw suppliers

MK8722 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: MK8722 is a systemic, direct pan-activator of AMP-activated protein kinase.

Technology Process of (3R,3aR,6R,6aR)-6-[[6-chloro-5-(4-phenylphenyl)-1H-imidazo[4,5-b]pyridin-2-yl]oxy]-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3-ol

There total 9 articles about (3R,3aR,6R,6aR)-6-[[6-chloro-5-(4-phenylphenyl)-1H-imidazo[4,5-b]pyridin-2-yl]oxy]-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3-ol 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:

5-([1,1′-biphenyl]-4-yl)-6-chloro-2-(methylsulfonyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazo[4,5-b]pyridine (1394373-53-5) + (3R,3aR,6R,6aS)-6-((tert-butyldimethylsilyl)oxy)hexahydrofuro[3,2-b]furan-3-ol (479541-48-5) → (3R,3aR,6R,6aR)-6-[[6-chloro-5-(4-phenylphenyl)-1H-imidazo[4,5-b]pyridin-2-yl]oxy]-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3-ol (1394371-71-1)

Guidance literature:

5-([1,1′-biphenyl]-4-yl)-6-chloro-2-(methylsulfonyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazo[4,5-b]pyridine; (3R,3aR,6R,6aS)-6-((tert-butyldimethylsilyl)oxy)hexahydrofuro[3,2-b]furan-3-ol; With 1,8-diazabicyclo[5.4.0]undec-7-ene; In N,N-dimethyl acetamide; at 22 ℃; for 18h;

With potassium hydrogensulfate; formic acid; at 22 ℃; for 18h;

With sodium hydroxide; In tetrahydrofuran; at 0 - 22 ℃; for 18h;

DOI:10.1021/acsmedchemlett.7b00417

Reference yield:

5-(biphenyl-4-yl)-6-chloro-2-(methylsulfonyl)-1H-imidazo[4,5-b]pyridine (1394373-37-5) → (3R,3aR,6R,6aR)-6-[[6-chloro-5-(4-phenylphenyl)-1H-imidazo[4,5-b]pyridin-2-yl]oxy]-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3-ol (1394371-71-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: triethylamine / tetrahydrofuran / 0.25 h / 0 - 22 °C

2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / N,N-dimethyl acetamide / 18 h / 22 °C

2.2: 18 h / 22 °C

2.3: 18 h / 0 - 22 °C

With 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In tetrahydrofuran; N,N-dimethyl acetamide;

DOI:10.1021/acsmedchemlett.7b00417

Reference yield:

2-amino-5,6-dichloro-3-nitropyridine (203794-33-6) → (3R,3aR,6R,6aR)-6-[[6-chloro-5-(4-phenylphenyl)-1H-imidazo[4,5-b]pyridin-2-yl]oxy]-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3-ol (1394371-71-1)

Guidance literature:

Multi-step reaction with 8 steps

1.1: acetic acid; sodium iodide / 2 h / 90 °C

2.1: tin(II) chloride dihdyrate / ethanol / 0.5 h / 70 °C

3.1: dmap / tetrahydrofuran / 1 h / 22 °C / Inert atmosphere

4.1: potassium hydroxide / ethanol / 0.5 h / 22 °C

4.2: 1 h / 22 °C

5.1: Oxone / acetonitrile; water / 18 h / 22 °C

6.1: potassium phosphate; palladium diacetate; di(adamantan-1-yl)(butyl)phosphine / tetrahydrofuran; water / 18 h / 45 °C

7.1: triethylamine / tetrahydrofuran / 0.25 h / 0 - 22 °C

8.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / N,N-dimethyl acetamide / 18 h / 22 °C

8.2: 18 h / 22 °C

8.3: 18 h / 0 - 22 °C

With dmap; Oxone; potassium phosphate; tin(II) chloride dihdyrate; di(adamantan-1-yl)(butyl)phosphine; palladium diacetate; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; sodium iodide; potassium hydroxide; In tetrahydrofuran; ethanol; N,N-dimethyl acetamide; water; acetonitrile;

DOI:10.1021/acsmedchemlett.7b00417

upstream raw materials:

5-(biphenyl-4-yl)-6-chloro-2-(methylsulfonyl)-1H-imidazo[4,5-b]pyridine

5-([1,1′-biphenyl]-4-yl)-6-chloro-2-(methylsulfonyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazo[4,5-b]pyridine

(3R,3aR,6R,6aS)-6-((tert-butyldimethylsilyl)oxy)hexahydrofuro[3,2-b]furan-3-ol

2-amino-5,6-dichloro-3-nitropyridine