N-(3-((4aS,5S,7aS)-2-amino-5-(fluoromethyl)-4a,5,7,7a-tetrahydro-4H-furo[3,4-d][1,3]thiazin-7a-yl)-4-fluorophenyl)-5-methoxypyrazine-2-carboxamide

Base Information

• Chemical Name: N-(3-((4aS,5S,7aS)-2-amino-5-(fluoromethyl)-4a,5,7,7a-tetrahydro-4H-furo[3,4-d][1,3]thiazin-7a-yl)-4-fluorophenyl)-5-methoxypyrazine-2-carboxamide
• CAS No.: 1391001-77-6
• Molecular Formula: C₁₉H₁₉F₂N₅O₃S
• Molecular Weight: 435.454
• Mol file: 1391001-77-6.mol

Synonyms:N-(3-((4aS,5S,7aS)-2-amino-5-(fluoromethyl)-4a,5,7,7a-tetrahydro-4H-furo[3,4-d][1,3]thiazin-7a-yl)-4-fluorophenyl)-5-methoxypyrazine-2-carboxamide

Chemical Property of N-(3-((4aS,5S,7aS)-2-amino-5-(fluoromethyl)-4a,5,7,7a-tetrahydro-4H-furo[3,4-d][1,3]thiazin-7a-yl)-4-fluorophenyl)-5-methoxypyrazine-2-carboxamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-(3-((4aS,5S,7aS)-2-amino-5-(fluoromethyl)-4a,5,7,7a-tetrahydro-4H-furo[3,4-d][1,3]thiazin-7a-yl)-4-fluorophenyl)-5-methoxypyrazine-2-carboxamide

There total 17 articles about N-(3-((4aS,5S,7aS)-2-amino-5-(fluoromethyl)-4a,5,7,7a-tetrahydro-4H-furo[3,4-d][1,3]thiazin-7a-yl)-4-fluorophenyl)-5-methoxypyrazine-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: 77.0%

N-(3-((4aS,5S,7aS)-2-benzamido-5-(fluoromethyl)-4a,5-dihydro-4H-furo[3,4-d][1,3]thiazin-7a(7H)-yl)-4-fluorophenyl)-5-methoxypyrazine-2-carboxamide → N-(3-((4aS,5S,7aS)-2-amino-5-(fluoromethyl)-4a,5,7,7a-tetrahydro-4H-furo[3,4-d][1,3]thiazin-7a-yl)-4-fluorophenyl)-5-methoxypyrazine-2-carboxamide (1391001-77-6)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In methanol; at 20 - 60 ℃; Inert atmosphere;

DOI:10.1021/acs.jmedchem.7b01769

Reference yield:

tert-butyl ((4aS,5S,7aS)-7a-(2-fluoro-5-(5-methoxypyrazine-2-carboxamido)phenyl)-5-(fluoromethyl)-4a,5,7,7a-tetrahydro-4H-furo[3,4-d][1,3]thiazin-2-yl)carbamate (1391001-95-8) → N-(3-((4aS,5S,7aS)-2-amino-5-(fluoromethyl)-4a,5,7,7a-tetrahydro-4H-furo[3,4-d][1,3]thiazin-7a-yl)-4-fluorophenyl)-5-methoxypyrazine-2-carboxamide (1391001-77-6)

Guidance literature:

tert-butyl ((4aS,5S,7aS)-7a-(2-fluoro-5-(5-methoxypyrazine-2-carboxamido)phenyl)-5-(fluoromethyl)-4a,5,7,7a-tetrahydro-4H-furo[3,4-d][1,3]thiazin-2-yl)carbamate; With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 2h;

With sodium hydrogencarbonate; In water; Saturated solution;

Reference yield:

tert-butyl (S)-2-((1-fluorobut-3-en-2-yl)oxy)acetate (1391001-87-8) → N-(3-((4aS,5S,7aS)-2-amino-5-(fluoromethyl)-4a,5,7,7a-tetrahydro-4H-furo[3,4-d][1,3]thiazin-7a-yl)-4-fluorophenyl)-5-methoxypyrazine-2-carboxamide (1391001-77-6)

Guidance literature:

Multi-step reaction with 14 steps

1.1: formic acid / 0 - 20 °C

2.1: 1,1'-carbonyldiimidazole / dichloromethane / 3 - 20 °C

2.2: 3 - 20 °C

3.1: n-butyllithium / hexane; tetrahydrofuran / -78 - -60 °C / Inert atmosphere

3.2: -78 - -60 °C

4.1: hydroxylamine hydrochloride; sodium acetate / methanol / 1.5 h / 50 °C

5.1: hydroquinone / xylene / 5 h / Reflux

6.1: zinc; acetic acid / 0 - 20 °C

7.1: dichloromethane / 18 h / 0 - 20 °C

8.1: trifluoromethylsulfonic anhydride; pyridine / dichloromethane / 2.08 h / 0 - 18 °C

9.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; methanol / 5 h / Reflux

10.1: nitric acid; trifluoroacetic acid; sulfuric acid / 0.92 h / 0 °C

10.2: pH 12

11.1: triethylamine / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

12.1: ethanol; tin(II) chloride dihdyrate / 20 °C

13.1: N-ethyl-N,N-diisopropylamine; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate / dichloromethane / 18 h / 20 °C

14.1: trifluoroacetic acid / dichloromethane / 2 h / 20 °C

14.2: Saturated solution

With pyridine; methanol; n-butyllithium; formic acid; tin(II) chloride dihdyrate; ethanol; trifluoromethylsulfonic anhydride; sulfuric acid; hydroxylamine hydrochloride; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; nitric acid; sodium acetate; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N-ethyl-N,N-diisopropylamine; hydroquinone; 1,1'-carbonyldiimidazole; trifluoroacetic acid; zinc; In tetrahydrofuran; methanol; hexane; dichloromethane; xylene;

upstream raw materials:

5-chloropyrazinoic acid

tert-butyl ((4aS,5S,7aS)-7a-(5-amino-2-fluorophenyl)-5-(fluoromethyl)-4a,5,7,7a-tetrahydro-4H-furo[3,4-d][1,3]thiazin-2-yl)carbamate

5-methoxy-pyrazine-2-carboxylic acid

tert-butyl (S)-2-((1-fluorobut-3-en-2-yl)oxy)acetate