N-{3-[(2R,3R)-5-amino-2-fluoro-3-methyl-3,6-dihydro-2H-1,4-oxazin-3-yl]-4-fluorophenyl}-5-chloropyridine-2-carboxamide

Base Information

Chemical Name:N-{3-[(2R,3R)-5-amino-2-fluoro-3-methyl-3,6-dihydro-2H-1,4-oxazin-3-yl]-4-fluorophenyl}-5-chloropyridine-2-carboxamide
CAS No.:1352416-52-4
Molecular Formula:C₁₇H₁₅ClF₂N₄O₂
Molecular Weight:380.782
Hs Code.:

Synonyms:N-{3-[(2R,3R)-5-amino-2-fluoro-3-methyl-3,6-dihydro-2H-1,4-oxazin-3-yl]-4-fluorophenyl}-5-chloropyridine-2-carboxamide

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Chemical Property of N-{3-[(2R,3R)-5-amino-2-fluoro-3-methyl-3,6-dihydro-2H-1,4-oxazin-3-yl]-4-fluorophenyl}-5-chloropyridine-2-carboxamide

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Technology Process of N-{3-[(2R,3R)-5-amino-2-fluoro-3-methyl-3,6-dihydro-2H-1,4-oxazin-3-yl]-4-fluorophenyl}-5-chloropyridine-2-carboxamide

There total 4 articles about N-{3-[(2R,3R)-5-amino-2-fluoro-3-methyl-3,6-dihydro-2H-1,4-oxazin-3-yl]-4-fluorophenyl}-5-chloropyridine-2-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: 76.0%

: 86873-60-1
5-chloropicolinic acid

: 1443259-43-5
(5R,6R)-5-(5-amino-2-fluorophenyl)-6-fluoro-5-methyl-5,6-dihydro-2H-1,4-oxazin-3-amine

: 1352416-52-4
N-{3-[(2R,3R)-5-amino-2-fluoro-3-methyl-3,6-dihydro-2H-1,4-oxazin-3-yl]-4-fluorophenyl}-5-chloropyridine-2-carboxamide

Guidance literature:: With 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride; In methanol; at 20 ℃; for 3h;
DOI:10.1021/acs.jmedchem.5b01101

Reference yield:

: (5R)-5-(5-bromo-2-fluorophenyl)-6-fluoro-5-methylmorpholine-3-thione

: 1352416-52-4
N-{3-[(2R,3R)-5-amino-2-fluoro-3-methyl-3,6-dihydro-2H-1,4-oxazin-3-yl]-4-fluorophenyl}-5-chloropyridine-2-carboxamide

Guidance literature:: Multi-step reaction with 3 steps

1: ammonia / methanol / 18 h / 60 °C / Sealed tube

2: sodium azide; copper(l) iodide; sodium carbonate; N,N-dimethylethylenediamine / dimethyl sulfoxide / 4 h / 110 °C

3: 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride / methanol / 3 h / 20 °C

With copper(l) iodide; sodium azide; ammonia; sodium carbonate; N,N-dimethylethylenediamine; 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride; In methanol; dimethyl sulfoxide; 2: |Buchwald-Hartwig Coupling;
DOI:10.1021/acs.jmedchem.5b01101

Reference yield:

: 1443259-41-3
(5R,6R)-5-(5-bromo-2-fluorophenyl)-6-fluoro-5-methyl-2,6-dihydro-1,4-oxazin-3-amine

: 1352416-52-4
N-{3-[(2R,3R)-5-amino-2-fluoro-3-methyl-3,6-dihydro-2H-1,4-oxazin-3-yl]-4-fluorophenyl}-5-chloropyridine-2-carboxamide

Guidance literature:: Multi-step reaction with 2 steps

1: sodium azide; copper(l) iodide; sodium carbonate; N,N-dimethylethylenediamine / dimethyl sulfoxide / 4 h / 110 °C

2: 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride / methanol / 3 h / 20 °C

With copper(l) iodide; sodium azide; sodium carbonate; N,N-dimethylethylenediamine; 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride; In methanol; dimethyl sulfoxide; 1: |Buchwald-Hartwig Coupling;
DOI:10.1021/acs.jmedchem.5b01101