2-amino-6-fluoro-N-[5-fluoro-4-(4-{[4-(oxetan-3-yl)piperazin-1-yl]carbonyl}piperidin-1-yl)pyridin-3-yl]pyrazolo[1,5-a]pyrimidine-3-carboxamide

Base Information

• Chemical Name: 2-amino-6-fluoro-N-[5-fluoro-4-(4-{[4-(oxetan-3-yl)piperazin-1-yl]carbonyl}piperidin-1-yl)pyridin-3-yl]pyrazolo[1,5-a]pyrimidine-3-carboxamide
• CAS No.: 1613191-99-3
• Molecular Formula: C₂₅H₂₉F₂N₉O₃
• Molecular Weight: 541.561
• Mol file: 1613191-99-3.mol

Synonyms:

Chemical Property of 2-amino-6-fluoro-N-[5-fluoro-4-(4-{[4-(oxetan-3-yl)piperazin-1-yl]carbonyl}piperidin-1-yl)pyridin-3-yl]pyrazolo[1,5-a]pyrimidine-3-carboxamide

Chemical Property:

Purity/Quality:

≥95% ^*data from raw suppliers

ATRinhibitor2 99.88% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-amino-6-fluoro-N-[5-fluoro-4-(4-{[4-(oxetan-3-yl)piperazin-1-yl]carbonyl}piperidin-1-yl)pyridin-3-yl]pyrazolo[1,5-a]pyrimidine-3-carboxamide

There total 19 articles about 2-amino-6-fluoro-N-[5-fluoro-4-(4-{[4-(oxetan-3-yl)piperazin-1-yl]carbonyl}piperidin-1-yl)pyridin-3-yl]pyrazolo[1,5-a]pyrimidine-3-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: 86.0%

1-(oxetan-3-yl)-piperazine (1254115-23-5) + 1-[3-[(2-amino-6-fluoro-pyrazolo[1,5-a]pyrimidine-3-carbonyl)amino]-5-fluoro-4-pyridyl]piperidine-4-carboxylic acid hydrochloride (1613192-04-3) → 2-amino-6-fluoro-N-[5-fluoro-4-(4-{[4-(oxetan-3-yl)piperazin-1-yl]carbonyl}piperidin-1-yl)pyridin-3-yl]pyrazolo[1,5-a]pyrimidine-3-carboxamide (1613191-99-3)

Guidance literature:

With N-[(6-chlorobenzotriazol-1-yl)oxy-(dimethylamino)methylene]-dimethyl-ammonium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; Solvent; Inert atmosphere;

Reference yield: 59.0%

1-(oxetan-3-yl)-piperazine (1254115-23-5) + 1-[3-[(2-amino-6-fluoropyrazolo[1,5-a]pyrimidine-3-carbonyl)amino]-5-fluoro-4-pyridyl]piperidine-4-carboxylic acid mesylate → 2-amino-6-fluoro-N-[5-fluoro-4-(4-{[4-(oxetan-3-yl)piperazin-1-yl]carbonyl}piperidin-1-yl)pyridin-3-yl]pyrazolo[1,5-a]pyrimidine-3-carboxamide (1613191-99-3)

Guidance literature:

With N-[(6-chlorobenzotriazol-1-yl)oxy-(dimethylamino)methylene]-dimethyl-ammonium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; Inert atmosphere;

Reference yield:

3-bromo-5-fluoropyridine (407-20-5) → 2-amino-6-fluoro-N-[5-fluoro-4-(4-{[4-(oxetan-3-yl)piperazin-1-yl]carbonyl}piperidin-1-yl)pyridin-3-yl]pyrazolo[1,5-a]pyrimidine-3-carboxamide (1613191-99-3)

Guidance literature:

Multi-step reaction with 6 steps

1.1: diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 2.17 h / -78 °C

1.2: -78 - 20 °C

2.1: sodium carbonate / cyclohexanol / 18 h / 120 °C / Inert atmosphere

3.1: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; Benzophenone imine; caesium carbonate / 1,4-dioxane / 95 °C / Inert atmosphere

3.2: 0.5 h / 20 °C

4.1: pyridine / 95 °C / Inert atmosphere

5.1: hydrogenchloride / water; 1,4-dioxane / Inert atmosphere

6.1: N-[(6-chlorobenzotriazol-1-yl)oxy-(dimethylamino)methylene]-dimethyl-ammonium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / Inert atmosphere

With hydrogenchloride; Benzophenone imine; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; n-butyllithium; N-[(6-chlorobenzotriazol-1-yl)oxy-(dimethylamino)methylene]-dimethyl-ammonium tetrafluoroborate; sodium carbonate; caesium carbonate; diisopropylamine; N-ethyl-N,N-diisopropylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In tetrahydrofuran; 1,4-dioxane; pyridine; hexane; water; cyclohexanol;

upstream raw materials:

benzyl 4-(oxetan-3-yl)piperazine-1-carboxylate

allyl 2-amino-6-fluoro-pyrazolo[1,5-a]pyrimidine-3-carboxylate

2-amino-6-fluoropyrazolo[1,5-a]pyrimidine-3-carboxylic acid

(6-chlorobenzotriazol-1-yl) 2-amino-6-fluoro-pyrazolo[1,5-a]pyrimidine-3-carboxylate