8-amino-2-(3-fluorophenyl)-N-(1-(oxetane-3-carbonyl)azetidin-3-yl)-1,7-naphthyridine-5-carboxamide

Base Information

• Chemical Name: 8-amino-2-(3-fluorophenyl)-N-(1-(oxetane-3-carbonyl)azetidin-3-yl)-1,7-naphthyridine-5-carboxamide
• CAS No.: 1449276-91-8
• Molecular Formula: C₂₂H₂₀FN₅O₃
• Molecular Weight: 421.431
• Mol file: 1449276-91-8.mol

Synonyms:8-amino-2-(3-fluorophenyl)-N-(1-(oxetane-3-carbonyl)azetidin-3-yl)-1,7-naphthyridine-5-carboxamide

Chemical Property of 8-amino-2-(3-fluorophenyl)-N-(1-(oxetane-3-carbonyl)azetidin-3-yl)-1,7-naphthyridine-5-carboxamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 8-amino-2-(3-fluorophenyl)-N-(1-(oxetane-3-carbonyl)azetidin-3-yl)-1,7-naphthyridine-5-carboxamide

There total 11 articles about 8-amino-2-(3-fluorophenyl)-N-(1-(oxetane-3-carbonyl)azetidin-3-yl)-1,7-naphthyridine-5-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: 10.0%

oxetane-3-carboxylic acid (114012-41-8) + 8-amino-N-(azetidin-3-yl)-2-(3-fluorophenyl)-1,7-naphthyridine-5-carboxamide trifluoroacetate (1449278-36-7) → 8-amino-2-(3-fluorophenyl)-N-(1-(oxetane-3-carbonyl)azetidin-3-yl)-1,7-naphthyridine-5-carboxamide (1449276-91-8)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; at 20 ℃; for 3h; Inert atmosphere;

Reference yield:

ethyl 8-amino-2-(3-fluorophenyl)-1,7-naphthyridine-5-carboxylate (1449277-90-0) → 8-amino-2-(3-fluorophenyl)-N-(1-(oxetane-3-carbonyl)azetidin-3-yl)-1,7-naphthyridine-5-carboxamide (1449276-91-8)

Guidance literature:

Multi-step reaction with 4 steps

1.1: water; sodium hydroxide / methanol / 2 h / 50 °C / Inert atmosphere

2.1: HATU; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.25 h / 20 °C / Inert atmosphere

2.2: 0.17 h / 20 °C / Inert atmosphere

3.1: dichloromethane / 20 °C / Inert atmosphere

4.1: HATU; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 3 h / 20 °C / Inert atmosphere

With water; N-ethyl-N,N-diisopropylamine; HATU; sodium hydroxide; In methanol; dichloromethane; N,N-dimethyl-formamide;

Reference yield:

5-bromo-7-(2-trimethylsilylethoxymethyl)-1,7-naphthyridin-8-one (1449278-46-9) → 8-amino-2-(3-fluorophenyl)-N-(1-(oxetane-3-carbonyl)azetidin-3-yl)-1,7-naphthyridine-5-carboxamide (1449276-91-8)

Guidance literature:

Multi-step reaction with 11 steps

1.1: potassium carbonate; N,N-dimethyl-formamide; palladium diacetate; 1,3-bis(dicyclohexylphosphine)propane / 3 h / 85 °C

2.1: urea hydrogen peroxide adduct / dichloromethane / 0.08 h / 20 °C / Inert atmosphere

2.2: 0.5 h / 20 °C / Inert atmosphere

3.1: oxalyl dichloride / dichloromethane / 0.5 h / 20 °C / Inert atmosphere

4.1: bis(di-tert-?butyl(4-?dimethylaminophenyl)?phosphine)?dichloropalladium(II); potassium phosphate / 1,4-dioxane; water / Inert atmosphere

5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere

6.1: trichlorophosphate / 3 h / 100 °C / Inert atmosphere

7.1: ammonia / isopropyl alcohol / 1.33 h / 140 °C / Inert atmosphere; Microwave irradiation

8.1: water; sodium hydroxide / methanol / 2 h / 50 °C / Inert atmosphere

9.1: HATU; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.25 h / 20 °C / Inert atmosphere

9.2: 0.17 h / 20 °C / Inert atmosphere

10.1: dichloromethane / 20 °C / Inert atmosphere

11.1: HATU; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 3 h / 20 °C / Inert atmosphere

With potassium phosphate; oxalyl dichloride; bis(di-tert-?butyl(4-?dimethylaminophenyl)?phosphine)?dichloropalladium(II); 1,3-bis(dicyclohexylphosphine)propane; tetrabutyl ammonium fluoride; ammonia; water; palladium diacetate; urea hydrogen peroxide adduct; potassium carbonate; N-ethyl-N,N-diisopropylamine; N,N-dimethyl-formamide; HATU; sodium hydroxide; trichlorophosphate; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; N,N-dimethyl-formamide; isopropyl alcohol;

upstream raw materials:

oxetane-3-carboxylic acid

8-amino-N-(azetidin-3-yl)-2-(3-fluorophenyl)-1,7-naphthyridine-5-carboxamide trifluoroacetate

ethyl 8-amino-2-(3-fluorophenyl)-1,7-naphthyridine-5-carboxylate

5-bromo-7-(2-trimethylsilylethoxymethyl)-1,7-naphthyridin-8-one