3-amino-oxetane-3-carboxylic acid ((R)-1-{5-[5-chloro-3-fluoro-2-(5-methyl-[1,2,4]oxadiazol-3-yl)-phenyl]-3-fluoro-pyridin-2-yl}-ethyl)-amide

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Chemical Name:3-amino-oxetane-3-carboxylic acid ((R)-1-{5-[5-chloro-3-fluoro-2-(5-methyl-[1,2,4]oxadiazol-3-yl)-phenyl]-3-fluoro-pyridin-2-yl}-ethyl)-amide
CAS No.:1384171-37-2
Molecular Formula:C₂₀H₁₈ClF₂N₅O₃
Molecular Weight:449.844
Hs Code.:

Synonyms:3-amino-oxetane-3-carboxylic acid ((R)-1-{5-[5-chloro-3-fluoro-2-(5-methyl-[1,2,4]oxadiazol-3-yl)-phenyl]-3-fluoro-pyridin-2-yl}-ethyl)-amide

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Chemical Property of 3-amino-oxetane-3-carboxylic acid ((R)-1-{5-[5-chloro-3-fluoro-2-(5-methyl-[1,2,4]oxadiazol-3-yl)-phenyl]-3-fluoro-pyridin-2-yl}-ethyl)-amide

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Technology Process of 3-amino-oxetane-3-carboxylic acid ((R)-1-{5-[5-chloro-3-fluoro-2-(5-methyl-[1,2,4]oxadiazol-3-yl)-phenyl]-3-fluoro-pyridin-2-yl}-ethyl)-amide

There total 15 articles about 3-amino-oxetane-3-carboxylic acid ((R)-1-{5-[5-chloro-3-fluoro-2-(5-methyl-[1,2,4]oxadiazol-3-yl)-phenyl]-3-fluoro-pyridin-2-yl}-ethyl)-amide 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: 75.0%

: 1384171-39-4
[3-((R)-1-{5-[5-chloro-3-fluoro-2-(5-methyl-[1,2,4]oxadiazol-3-yl)-phenyl]-3-fluoro-pyridin-2-yl}-ethylcarbamoyl)-oxetan-3-yl]-carbamic acid 9H-fluoren-9-ylmethyl ester

: 1384171-37-2
3-amino-oxetane-3-carboxylic acid ((R)-1-{5-[5-chloro-3-fluoro-2-(5-methyl-[1,2,4]oxadiazol-3-yl)-phenyl]-3-fluoro-pyridin-2-yl}-ethyl)-amide

Guidance literature:: With piperidine; In dichloromethane; at 20 ℃; for 1h;

Reference yield:

: 573675-25-9
5-bromo-3-nitropyridine-2-carbonitrile

: 1384171-37-2
3-amino-oxetane-3-carboxylic acid ((R)-1-{5-[5-chloro-3-fluoro-2-(5-methyl-[1,2,4]oxadiazol-3-yl)-phenyl]-3-fluoro-pyridin-2-yl}-ethyl)-amide

Guidance literature:: Multi-step reaction with 8 steps

1.1: tetrabutyl ammonium fluoride; sulfuric acid / N,N-dimethyl-formamide / 1 h / -40 °C

1.2: -40 °C / pH 3

2.1: methylmagnesium chloride / toluene; tetrahydrofuran / 1 h / -10 °C

2.2: 16 h / 25 °C

2.3: 0.5 h

3.1: hydrogen / (1S,1S',2R,2R')-1,1'-di-tert-butyl-(2,2’)-diphospholane; bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate / methanol / 4.5 h / 7500.75 Torr / Autoclave; Charcoal presence

4.1: potassium acetate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / dichloromethane; dimethyl sulfoxide / 1.67 h / 90 °C / Inert atmosphere; Sealed tube

5.1: potassium carbonate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / dichloromethane / 3 h / 20 - 80 °C / Inert atmosphere; Sealed tube

6.1: hydrogenchloride / water / 75 °C

6.2: pH 12

7.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 0.08 h / 20 °C

7.2: 1.5 h / 20 °C

8.1: piperidine / dichloromethane / 1 h / 20 °C

With piperidine; hydrogenchloride; sulfuric acid; tetrabutyl ammonium fluoride; hydrogen; methylmagnesium chloride; potassium acetate; potassium carbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate; (1S,1S',2R,2R')-1,1'-di-tert-butyl-(2,2’)-diphospholane; In tetrahydrofuran; methanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; 5.1: Suzuki Coupling;

Reference yield:

: 15862-37-0
2,5-dibromo-3-nitro-pyridine

: 1384171-37-2
3-amino-oxetane-3-carboxylic acid ((R)-1-{5-[5-chloro-3-fluoro-2-(5-methyl-[1,2,4]oxadiazol-3-yl)-phenyl]-3-fluoro-pyridin-2-yl}-ethyl)-amide

Guidance literature:: Multi-step reaction with 9 steps

1.1: propiononitrile / 17 h / 90 °C

2.1: tetrabutyl ammonium fluoride; sulfuric acid / N,N-dimethyl-formamide / 1 h / -40 °C

2.2: -40 °C / pH 3

3.1: methylmagnesium chloride / toluene; tetrahydrofuran / 1 h / -10 °C

3.2: 16 h / 25 °C

3.3: 0.5 h

4.1: hydrogen / (1S,1S',2R,2R')-1,1'-di-tert-butyl-(2,2’)-diphospholane; bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate / methanol / 4.5 h / 7500.75 Torr / Autoclave; Charcoal presence

5.1: potassium acetate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / dichloromethane; dimethyl sulfoxide / 1.67 h / 90 °C / Inert atmosphere; Sealed tube

6.1: potassium carbonate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / dichloromethane / 3 h / 20 - 80 °C / Inert atmosphere; Sealed tube

7.1: hydrogenchloride / water / 75 °C

7.2: pH 12

8.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 0.08 h / 20 °C

8.2: 1.5 h / 20 °C

9.1: piperidine / dichloromethane / 1 h / 20 °C

With piperidine; hydrogenchloride; sulfuric acid; tetrabutyl ammonium fluoride; hydrogen; methylmagnesium chloride; potassium acetate; potassium carbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate; (1S,1S',2R,2R')-1,1'-di-tert-butyl-(2,2’)-diphospholane; In tetrahydrofuran; methanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; propiononitrile; 6.1: Suzuki Coupling;