5-chloro-3-methoxymethyl-pyridine-2-carboxylic acid [3-((R)-5-amino-3-difluoromethyl-3,6-dihydro-2H-[1,4]oxazin-3-yl)-4-fluoro-phenyl]-amide

Base Information

Chemical Name:5-chloro-3-methoxymethyl-pyridine-2-carboxylic acid [3-((R)-5-amino-3-difluoromethyl-3,6-dihydro-2H-[1,4]oxazin-3-yl)-4-fluoro-phenyl]-amide
CAS No.:1386984-01-5
Molecular Formula:C₁₉H₁₈ClF₃N₄O₃
Molecular Weight:442.825
Hs Code.:

Synonyms:5-chloro-3-methoxymethyl-pyridine-2-carboxylic acid [3-((R)-5-amino-3-difluoromethyl-3,6-dihydro-2H-[1,4]oxazin-3-yl)-4-fluoro-phenyl]-amide

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Chemical Property of 5-chloro-3-methoxymethyl-pyridine-2-carboxylic acid [3-((R)-5-amino-3-difluoromethyl-3,6-dihydro-2H-[1,4]oxazin-3-yl)-4-fluoro-phenyl]-amide

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Technology Process of 5-chloro-3-methoxymethyl-pyridine-2-carboxylic acid [3-((R)-5-amino-3-difluoromethyl-3,6-dihydro-2H-[1,4]oxazin-3-yl)-4-fluoro-phenyl]-amide

There total 20 articles about 5-chloro-3-methoxymethyl-pyridine-2-carboxylic acid [3-((R)-5-amino-3-difluoromethyl-3,6-dihydro-2H-[1,4]oxazin-3-yl)-4-fluoro-phenyl]-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:

: 1386985-56-3
((R)-5-{5-[(5-chloro-3-methoxymethyl-pyridine-2-carbonyl)-amino]-2-fluoro-phenyl}-5-difluoromethyl-5,6-dihydro-2H-[1,4]oxazin-3-yl)-carbamic acid tert-butyl ester

: 1386984-01-5
5-chloro-3-methoxymethyl-pyridine-2-carboxylic acid [3-((R)-5-amino-3-difluoromethyl-3,6-dihydro-2H-[1,4]oxazin-3-yl)-4-fluoro-phenyl]-amide

Guidance literature:: ((R)-5-{5-[(5-chloro-3-methoxymethyl-pyridine-2-carbonyl)-amino]-2-fluoro-phenyl}-5-difluoromethyl-5,6-dihydro-2H-[1,4]oxazin-3-yl)-carbamic acid tert-butyl ester; With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 18h;

With ammonia; In water; ethyl acetate; Cooling with ice;

Reference yield:

: 558465-93-3
(2,5-dichloro-3-pyridinyl)methanol

: 1386984-01-5
5-chloro-3-methoxymethyl-pyridine-2-carboxylic acid [3-((R)-5-amino-3-difluoromethyl-3,6-dihydro-2H-[1,4]oxazin-3-yl)-4-fluoro-phenyl]-amide

Guidance literature:: Multi-step reaction with 5 steps

1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.25 h / 0 °C

1.2: 20 °C

2.1: zinc / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / N,N-dimethyl-formamide / 2 h / 150 °C / Inert atmosphere

3.1: sodium hydroxide; water / 4 h / 100 °C

3.2: pH 5 - 6

4.1: 1-hydroxy-7-aza-benzotriazole; N-ethyl-N,N-diisopropylamine; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide / N,N-dimethyl-formamide / 20 h / 20 °C

5.1: trifluoroacetic acid / dichloromethane / 18 h / 20 °C

5.2: Cooling with ice

With 1-hydroxy-7-aza-benzotriazole; water; sodium hydride; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; sodium hydroxide; zinc; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; In dichloromethane; N,N-dimethyl-formamide; mineral oil;

Reference yield:

: 460-00-4
1-Bromo-4-fluorobenzene

: 1386984-01-5
5-chloro-3-methoxymethyl-pyridine-2-carboxylic acid [3-((R)-5-amino-3-difluoromethyl-3,6-dihydro-2H-[1,4]oxazin-3-yl)-4-fluoro-phenyl]-amide

Guidance literature:: Multi-step reaction with 16 steps

1.1: diisopropylamine; n-butyllithium / hexane; tetrahydrofuran / 2.5 h / -70 - -60 °C

1.2: -70 - -40 °C

1.3: -40 °C

2.1: toluene / 18 h / 90 °C

3.1: tetrahydrofuran / 1 h / -70 - 0 °C

3.2: 0 °C

4.1: sodium hydrogencarbonate; ozone / dichloromethane; methanol / -78 °C

4.2: 0.67 h / -78 - 0 °C

5.1: hydrogenchloride / 1,4-dioxane / 2 h / 20 °C

6.1: sodium hydrogencarbonate / dichloromethane; water / Cooling with ice

6.2: Cooling with ice

7.1: potassium tert-butylate / tert-butyl alcohol / 3 h / Reflux

8.1: hydrogen; sodium acetate / palladium 10% on activated carbon / methanol / 1 h / 20 °C

9.1: Lawessons reagent / tetrahydrofuran / 1 h / 68 °C

10.1: ammonia / methanol

10.3: Cooling with ice

11.1: potassium nitrate; sulfuric acid / 1 h / 22 °C

11.2: pH 12 - 14 / Cooling with ice

12.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 82 h / 20 - 60 °C

13.1: hydrogen / palladium 10% on activated carbon / tetrahydrofuran / 6 h / 20 °C

14.1: Chiralpak AD-H / n-heptane; ethanol; methanol / Resolution of racemate

15.1: 1-hydroxy-7-aza-benzotriazole; N-ethyl-N,N-diisopropylamine; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide / N,N-dimethyl-formamide / 20 h / 20 °C

16.1: trifluoroacetic acid / dichloromethane / 18 h / 20 °C

16.2: Cooling with ice

With Lawessons reagent; hydrogenchloride; n-butyllithium; 1-hydroxy-7-aza-benzotriazole; sulfuric acid; potassium tert-butylate; ammonia; hydrogen; sodium acetate; sodium hydrogencarbonate; ozone; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; potassium nitrate; diisopropylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; palladium 10% on activated carbon; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; hexane; n-heptane; dichloromethane; water; N,N-dimethyl-formamide; toluene; tert-butyl alcohol;