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

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Chemical Name:N-{3-[(3R)-5-amino-3-methyl-3,6-dihydro-2H-1,4-oxazin-3-yl]-4-fluorophenyl}-5-chloropyridine-2-carboxamide
CAS No.:1266786-51-9
Molecular Formula:C₁₇H₁₆ClFN₄O₂
Molecular Weight:362.791
Hs Code.:

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

There total 12 articles about N-{3-[(3R)-5-amino-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: 78.0%

: 86873-60-1
5-chloropicolinic acid

: 1266785-90-3
(5R)-5-(5-amino-2-fluorophenyl)-5-methyl-5,6-dihydro-2H-1,4-oxazin-3-amine

: 1266786-51-9
N-{3-[(3R)-5-amino-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:

: 1266784-18-2
rac-2-amino-2-(5-bromo-2-fluoro-phenyl)-propionic acid methyl ester

: 1266786-51-9
N-{3-[(3R)-5-amino-3-methyl-3,6-dihydro-2H-1,4-oxazin-3-yl]-4-fluorophenyl}-5-chloropyridine-2-carboxamide

Guidance literature:: Multi-step reaction with 8 steps

1.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / -15 - 0 °C

2.1: Chiralpak Diacel AD / methanol / Supercritical conditions

3.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 0.5 h / -78 °C

3.2: 1.5 h / -15 - 0 °C

4.1: tetraphosphorus decasulfide / tetrahydrofuran / 0.83 h / 50 °C

5.1: ammonium hydroxide / 4 h / 60 °C / Sealed tube

6.1: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate / toluene / 20 °C / Sealed tube; Inert atmosphere

6.2: 2 h / 100 °C

6.3: 0.5 h / 20 °C

7.1: ammonia / methanol

8.1: 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride / methanol / 3 h / 20 °C

With ammonium hydroxide; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; lithium aluminium tetrahydride; tetraphosphorus decasulfide; ammonia; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; N-ethyl-N,N-diisopropylamine; 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride; sodium t-butanolate; In tetrahydrofuran; methanol; toluene; 3.2: |Williamson Ether Synthesis;
DOI:10.1021/acs.jmedchem.5b01101

Reference yield:

: 1266784-23-9
(RS)-2-amino-2-(5-bromo-2-fluoro-phenyl)-propionic acid

: 1266786-51-9
N-{3-[(3R)-5-amino-3-methyl-3,6-dihydro-2H-1,4-oxazin-3-yl]-4-fluorophenyl}-5-chloropyridine-2-carboxamide

Guidance literature:: Multi-step reaction with 9 steps

1.1: sulfuric acid / methanol / Reflux

2.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / -15 - 0 °C

3.1: Chiralpak Diacel AD / methanol / Supercritical conditions

4.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 0.5 h / -78 °C

4.2: 1.5 h / -15 - 0 °C

5.1: tetraphosphorus decasulfide / tetrahydrofuran / 0.83 h / 50 °C

6.1: ammonium hydroxide / 4 h / 60 °C / Sealed tube

7.1: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate / toluene / 20 °C / Sealed tube; Inert atmosphere

7.2: 2 h / 100 °C

7.3: 0.5 h / 20 °C

8.1: ammonia / methanol

9.1: 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride / methanol / 3 h / 20 °C

With ammonium hydroxide; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; lithium aluminium tetrahydride; tetraphosphorus decasulfide; sulfuric acid; ammonia; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; N-ethyl-N,N-diisopropylamine; 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride; sodium t-butanolate; In tetrahydrofuran; methanol; toluene; 4.2: |Williamson Ether Synthesis;
DOI:10.1021/acs.jmedchem.5b01101