rac-5-chloropyridine-2-carboxylic acid [3-(6-amino-2,4-dimethyl-5-oxo-2,3,4,5-tetrahydropyrazin-2-yl)-4-fluorophenyl]amide

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Chemical Name:rac-5-chloropyridine-2-carboxylic acid [3-(6-amino-2,4-dimethyl-5-oxo-2,3,4,5-tetrahydropyrazin-2-yl)-4-fluorophenyl]amide
CAS No.:1313525-58-4
Molecular Formula:C₁₈H₁₇ClFN₅O₂
Molecular Weight:389.817
Hs Code.:

Synonyms:

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Chemical Property of rac-5-chloropyridine-2-carboxylic acid [3-(6-amino-2,4-dimethyl-5-oxo-2,3,4,5-tetrahydropyrazin-2-yl)-4-fluorophenyl]amide

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Technology Process of rac-5-chloropyridine-2-carboxylic acid [3-(6-amino-2,4-dimethyl-5-oxo-2,3,4,5-tetrahydropyrazin-2-yl)-4-fluorophenyl]amide

There total 14 articles about rac-5-chloropyridine-2-carboxylic acid [3-(6-amino-2,4-dimethyl-5-oxo-2,3,4,5-tetrahydropyrazin-2-yl)-4-fluorophenyl]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: 25.0%

: 86873-60-1
5-chloropicolinic acid

: 1350523-58-8
rac-3-amino-5-(5-amino-2-fluoro-phenyl)-1,5-dimethyl-5,6-dihydro-1H-pyrazin-2-one

: 1313525-58-4,1350523-67-9,1350523-69-1
rac-5-chloropyridine-2-carboxylic acid [3-(6-amino-2,4-dimethyl-5-oxo-2,3,4,5-tetrahydropyrazin-2-yl)-4-fluorophenyl]amide

Guidance literature:: With 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride; In methanol; at 0 ℃; for 3h;
DOI:10.1016/j.bmcl.2011.10.050

Reference yield:

: 1313525-88-0
rac-3-amino-5-(5-bromo-2-fluoro-phenyl)-1,5-dimethyl-5,6-dihydro-1H-pyrazin-2-one

: 1313525-58-4,1350523-67-9,1350523-69-1
rac-5-chloropyridine-2-carboxylic acid [3-(6-amino-2,4-dimethyl-5-oxo-2,3,4,5-tetrahydropyrazin-2-yl)-4-fluorophenyl]amide

Guidance literature:: Multi-step reaction with 2 steps

1: copper(l) iodide; sodium azide; bis 1,2-(dimethylamino)ethylene; sodium carbonate / dimethyl sulfoxide / 1 h / 110 °C

2: 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride / methanol / 3 h / 0 °C

With copper(l) iodide; sodium azide; bis 1,2-(dimethylamino)ethylene; sodium carbonate; 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride; In methanol; dimethyl sulfoxide;
DOI:10.1016/j.bmcl.2011.10.050

Reference yield:

: 198477-89-3
1-(5-bromo-2-fluorophenyl)ethan-1-one

: 1313525-58-4,1350523-67-9,1350523-69-1
rac-5-chloropyridine-2-carboxylic acid [3-(6-amino-2,4-dimethyl-5-oxo-2,3,4,5-tetrahydropyrazin-2-yl)-4-fluorophenyl]amide

Guidance literature:: Multi-step reaction with 14 steps

1: ammonia; ammonium chloride / methanol / 96 h / 20 °C

2: hydrogenchloride; water / 18 h / Reflux

3: sulfuric acid / 48 h

4: sodium tetrahydroborate / ethanol / 3 h / 20 °C

5: sodium hydrogencarbonate / tetrahydrofuran / 15 h / 0 °C

6: Dess-Martin periodane / dichloromethane / 1 h / 0 - 20 °C

7: acetic acid / tetrahydrofuran; dichloromethane / 1 h / 20 °C

8: sodium triacetoxy borohydride / 2 h / 20 °C

9: N-ethyl-N,N-diisopropylamine / dichloromethane / 3 h / 0 °C

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

11: dichloromethane / 72 h / 20 °C

12: ammonia; ammonium chloride / ethanol / 18 h / 75 °C

13: copper(l) iodide; sodium azide; bis 1,2-(dimethylamino)ethylene; sodium carbonate / dimethyl sulfoxide / 1 h / 110 °C

14: 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride / methanol / 3 h / 0 °C

With sodium triacetoxy borohydride; hydrogenchloride; sodium tetrahydroborate; copper(l) iodide; sodium azide; sulfuric acid; bis 1,2-(dimethylamino)ethylene; ammonia; water; sodium hydrogencarbonate; sodium carbonate; ammonium chloride; Dess-Martin periodane; acetic acid; N-ethyl-N,N-diisopropylamine; 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; dimethyl sulfoxide; 1: Strecker reaction;
DOI:10.1016/j.bmcl.2011.10.050