1-(4-fluorophenyl)-4-[(S)-1-(2-methanesulfonyl-pyridin-4-yl)-butylcarbamoyl]-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-b]pyridine-6-carboxylic acid

Base Information

• Chemical Name: 1-(4-fluorophenyl)-4-[(S)-1-(2-methanesulfonyl-pyridin-4-yl)-butylcarbamoyl]-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-b]pyridine-6-carboxylic acid
• CAS No.: 1383733-70-7
• Molecular Formula: C₂₄H₂₆FN₅O₅S
• Molecular Weight: 515.565
• Mol file: 1383733-70-7.mol

Synonyms:1-(4-fluorophenyl)-4-[(S)-1-(2-methanesulfonyl-pyridin-4-yl)-butylcarbamoyl]-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-b]pyridine-6-carboxylic acid

Chemical Property of 1-(4-fluorophenyl)-4-[(S)-1-(2-methanesulfonyl-pyridin-4-yl)-butylcarbamoyl]-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-b]pyridine-6-carboxylic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-(4-fluorophenyl)-4-[(S)-1-(2-methanesulfonyl-pyridin-4-yl)-butylcarbamoyl]-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-b]pyridine-6-carboxylic acid

There total 12 articles about 1-(4-fluorophenyl)-4-[(S)-1-(2-methanesulfonyl-pyridin-4-yl)-butylcarbamoyl]-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-b]pyridine-6-carboxylic 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:

5-bromo-2-chloro-3-nitropyridine (67443-38-3) → 1-(4-fluorophenyl)-4-[(S)-1-(2-methanesulfonyl-pyridin-4-yl)-butylcarbamoyl]-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-b]pyridine-6-carboxylic acid (1383733-70-7)

Guidance literature:

Multi-step reaction with 12 steps

1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / -10 °C

1.2: 4 h

2.1: hydrogenchloride / water / 4 h / Reflux

3.1: acetic acid; iron / 2 h / Reflux

4.1: triethylamine / dichloromethane / 18 h

4.2: 1 h

5.1: acetic anhydride; potassium acetate; acetic acid; isopentyl nitrite / toluene / 3 h / Reflux

6.1: potassium carbonate; methanol / 1 h / Reflux

7.1: N-ethyl-N,N-diisopropylamine / bis(benzonitrile)palladium(II) dichloride; 1,1'-bis-(diphenylphosphino)ferrocene / 4 h / 135 °C / 11251.1 Torr

8.1: potassium carbonate / cis-N,N'-dimethyl-1,2-diaminocyclohexane; copper(l) iodide / N,N-dimethyl-formamide / 3 h / 130 °C / microwave irradiation

9.1: hydrogenchloride; hydrogen / platinum(IV) oxide hydrate / 1,4-dioxane; ethanol / 18 h / 760.05 Torr

10.1: sodium hydrogencarbonate / dichloromethane; toluene; water / 1 h / 0 °C

11.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 18 h

12.1: sodium hydroxide; water / methanol / 4 h

12.2: pH 4

With hydrogenchloride; methanol; water; hydrogen; potassium acetate; acetic anhydride; iron; sodium hydride; sodium hydrogencarbonate; potassium carbonate; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; sodium hydroxide; isopentyl nitrite; 1,1'-bis-(diphenylphosphino)ferrocene; copper(l) iodide; bis(benzonitrile)palladium(II) dichloride; platinum(IV) oxide hydrate; cis-N,N'-dimethyl-1,2-diaminocyclohexane; In 1,4-dioxane; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; mineral oil;

Reference yield:

1-(4-fluorophenyl)-4-[(S)-1-(2-methanesulfonyl-pyridin-4-yl)-butylcarbamoyl]-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-b]pyridine-6-carboxylic acid ethyl ester (1383733-69-4) → 1-(4-fluorophenyl)-4-[(S)-1-(2-methanesulfonyl-pyridin-4-yl)-butylcarbamoyl]-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-b]pyridine-6-carboxylic acid (1383733-70-7)

Guidance literature:

1-(4-fluorophenyl)-4-[(S)-1-(2-methanesulfonyl-pyridin-4-yl)-butylcarbamoyl]-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-b]pyridine-6-carboxylic acid ethyl ester; With water; sodium hydroxide; In methanol; for 4h;

With hydrogenchloride; In water; pH=4;

Reference yield:

2-(5-bromo-3-nitro-pyridin-2-yl)-malonic acid diethyl ester (911434-04-3) → 1-(4-fluorophenyl)-4-[(S)-1-(2-methanesulfonyl-pyridin-4-yl)-butylcarbamoyl]-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-b]pyridine-6-carboxylic acid (1383733-70-7)

Guidance literature:

Multi-step reaction with 11 steps

1.1: hydrogenchloride / water / 4 h / Reflux

2.1: acetic acid; iron / 2 h / Reflux

3.1: triethylamine / dichloromethane / 18 h

3.2: 1 h

4.1: acetic anhydride; potassium acetate; acetic acid; isopentyl nitrite / toluene / 3 h / Reflux

5.1: potassium carbonate; methanol / 1 h / Reflux

6.1: N-ethyl-N,N-diisopropylamine / bis(benzonitrile)palladium(II) dichloride; 1,1'-bis-(diphenylphosphino)ferrocene / 4 h / 135 °C / 11251.1 Torr

7.1: potassium carbonate / cis-N,N'-dimethyl-1,2-diaminocyclohexane; copper(l) iodide / N,N-dimethyl-formamide / 3 h / 130 °C / microwave irradiation

8.1: hydrogenchloride; hydrogen / platinum(IV) oxide hydrate / 1,4-dioxane; ethanol / 18 h / 760.05 Torr

9.1: sodium hydrogencarbonate / dichloromethane; toluene; water / 1 h / 0 °C

10.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 18 h

11.1: sodium hydroxide; water / methanol / 4 h

11.2: pH 4

With hydrogenchloride; methanol; water; hydrogen; potassium acetate; acetic anhydride; iron; sodium hydrogencarbonate; potassium carbonate; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; sodium hydroxide; isopentyl nitrite; 1,1'-bis-(diphenylphosphino)ferrocene; copper(l) iodide; bis(benzonitrile)palladium(II) dichloride; platinum(IV) oxide hydrate; cis-N,N'-dimethyl-1,2-diaminocyclohexane; In 1,4-dioxane; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene;

upstream raw materials:

2-(5-bromo-3-nitro-pyridin-2-yl)-malonic acid diethyl ester

5-bromo-2-methyl-3-nitropyridine

5-bromo-2-methylpyridin-3-ylamine

6-bromo-1H-pyrazolo[4,3-b]pyridine

Downstream raw materials:

1-(4-fluorophenyl)-l,5,6,7-tetrahydro-pyrazolo[4,3-b]pyridine-4,6-dicarboxylic acid 4-{[(S)-1-(2-methanesulfonyl-pyridin-4-yl)-butyl]-amide} 6-methylamide

Refernces