N-{4-[(3S)-3-aminopiperidin-1-yl]thieno[2,3-b]pyridin-5-yl}-2-(2,6-difluorophenyl)-1,3-thiazole-4-carboxamide

Base Information

• Chemical Name: N-{4-[(3S)-3-aminopiperidin-1-yl]thieno[2,3-b]pyridin-5-yl}-2-(2,6-difluorophenyl)-1,3-thiazole-4-carboxamide
• CAS No.: 1620011-10-0
• Molecular Formula: C₂₂H₁₉F₂N₅OS₂
• Molecular Weight: 471.555
• Mol file: 1620011-10-0.mol

Synonyms:N-{4-[(3S)-3-aminopiperidin-1-yl]thieno[2,3-b]pyridin-5-yl}-2-(2,6-difluorophenyl)-1,3-thiazole-4-carboxamide

Chemical Property of N-{4-[(3S)-3-aminopiperidin-1-yl]thieno[2,3-b]pyridin-5-yl}-2-(2,6-difluorophenyl)-1,3-thiazole-4-carboxamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-{4-[(3S)-3-aminopiperidin-1-yl]thieno[2,3-b]pyridin-5-yl}-2-(2,6-difluorophenyl)-1,3-thiazole-4-carboxamide

There total 8 articles about N-{4-[(3S)-3-aminopiperidin-1-yl]thieno[2,3-b]pyridin-5-yl}-2-(2,6-difluorophenyl)-1,3-thiazole-4-carboxamide 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: 34.0%

tert-butyl {(3S)-1-[5-({[2-(2,6-difluorophenyl)-1,3-thiazol-4-yl]carbonyl}amino)thieno[2,3-b]pyridin-4-yl]piperidin-3-yl}carbamate (1620011-11-1) → N-{4-[(3S)-3-aminopiperidin-1-yl]thieno[2,3-b]pyridin-5-yl}-2-(2,6-difluorophenyl)-1,3-thiazole-4-carboxamide (1620011-10-0)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 20 - 30 ℃; for 0.5h;

Reference yield:

2-(2,6-difluorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (863868-37-5) → N-{4-[(3S)-3-aminopiperidin-1-yl]thieno[2,3-b]pyridin-5-yl}-2-(2,6-difluorophenyl)-1,3-thiazole-4-carboxamide (1620011-10-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: bis(tri-t-butylphosphine)palladium⁽⁰⁾; N-ethyl-N,N-diisopropylamine / water; 1,4-dioxane / 3 h / 120 °C / Inert atmosphere

2.1: lithium hydroxide monohydrate / water; tetrahydrofuran / 5 h / 60 °C

3.1: dichloromethane / 2 h / 20 - 30 °C

3.2: 2 h / 20 - 30 °C

4.1: trifluoroacetic acid / dichloromethane / 0.5 h / 20 - 30 °C

With bis(tri-t-butylphosphine)palladium⁽⁰⁾; lithium hydroxide monohydrate; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water;

Reference yield:

ethyl 2-(2,6-difluorophenyl)-1,3-thiazole-4-carboxylate (1187056-38-7) → N-{4-[(3S)-3-aminopiperidin-1-yl]thieno[2,3-b]pyridin-5-yl}-2-(2,6-difluorophenyl)-1,3-thiazole-4-carboxamide (1620011-10-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: lithium hydroxide monohydrate / water; tetrahydrofuran / 5 h / 60 °C

2.1: dichloromethane / 2 h / 20 - 30 °C

2.2: 2 h / 20 - 30 °C

3.1: trifluoroacetic acid / dichloromethane / 0.5 h / 20 - 30 °C

With lithium hydroxide monohydrate; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; water;

upstream raw materials:

2-(2,6-difluorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

ethyl 2-(2,6-difluorophenyl)-1,3-thiazole-4-carboxylate

2-(2,6-difluorophenyl)-1,3-thiazole-4-carboxylic acid

tert-butyl [(3S)-1-(5-aminothieno[2,3-b]pyridin-4-yl)piperidin-3-yl]carbamate