N-[(4aR,8aS)-8a-(2,4-difluorophenyl)-6-(5-fluoro-1-methyl-1H-pyrazol-3-yl)-4,4a,8,8a-tetrahydropyrano[3,4-d][1,3]thiazin-2-yl]benzamide

Base Information

• Chemical Name: N-[(4aR,8aS)-8a-(2,4-difluorophenyl)-6-(5-fluoro-1-methyl-1H-pyrazol-3-yl)-4,4a,8,8a-tetrahydropyrano[3,4-d][1,3]thiazin-2-yl]benzamide
• CAS No.: 1621585-56-5
• Molecular Formula: C₂₄H₁₉F₃N₄O₂S
• Molecular Weight: 484.502
• Mol file: 1621585-56-5.mol

Synonyms:N-[(4aR,8aS)-8a-(2,4-difluorophenyl)-6-(5-fluoro-1-methyl-1H-pyrazol-3-yl)-4,4a,8,8a-tetrahydropyrano[3,4-d][1,3]thiazin-2-yl]benzamide

Chemical Property of N-[(4aR,8aS)-8a-(2,4-difluorophenyl)-6-(5-fluoro-1-methyl-1H-pyrazol-3-yl)-4,4a,8,8a-tetrahydropyrano[3,4-d][1,3]thiazin-2-yl]benzamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-[(4aR,8aS)-8a-(2,4-difluorophenyl)-6-(5-fluoro-1-methyl-1H-pyrazol-3-yl)-4,4a,8,8a-tetrahydropyrano[3,4-d][1,3]thiazin-2-yl]benzamide

There total 13 articles about N-[(4aR,8aS)-8a-(2,4-difluorophenyl)-6-(5-fluoro-1-methyl-1H-pyrazol-3-yl)-4,4a,8,8a-tetrahydropyrano[3,4-d][1,3]thiazin-2-yl]benzamide 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: 89.0%

5-fluoro-3-iodo-1-methyl-1H-pyrazole (1621585-53-2) + (4aR,8aS)-2-(benzoylamino)-8a-(2,4-difluorophenyl)-4,4a,8,8a-tetrahydropyrano[3,4-d][1,3]thiazin-6-yl trifluoromethanesulfonate (1621585-55-4) → N-[(4aR,8aS)-8a-(2,4-difluorophenyl)-6-(5-fluoro-1-methyl-1H-pyrazol-3-yl)-4,4a,8,8a-tetrahydropyrano[3,4-d][1,3]thiazin-2-yl]benzamide (1621585-56-5)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; bis(tri-n-butyltin); In N,N-dimethyl-formamide; at 120 ℃; for 0.25h; Inert atmosphere;

Reference yield:

2-{[(2R)-1-(benzyloxy)pent-4-en-2-yl]oxy}-N-hydroxyethanimine (1220328-95-9) → N-[(4aR,8aS)-8a-(2,4-difluorophenyl)-6-(5-fluoro-1-methyl-1H-pyrazol-3-yl)-4,4a,8,8a-tetrahydropyrano[3,4-d][1,3]thiazin-2-yl]benzamide (1621585-56-5)

Guidance literature:

Multi-step reaction with 11 steps

1.1: sodium hypochlorite / water; dichloromethane / 1.5 h / 0 - 15 °C

2.1: boron trifluoride diethyl etherate / toluene; di-isopropyl ether / 0.5 h / -76 °C

2.2: 1.5 h / -76 - -71 °C

3.1: zinc; acetic acid / 16 h / 20 - 40 °C

4.1: dichloromethane / 18 h / 20 °C

5.1: pyridine; trifluoromethylsulfonic anhydride / dichloromethane / 3 h / -60 - -5 °C

6.1: boron trichloride / dichloromethane; n-heptane / 4.25 h / 0 - 20 °C

7.1: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / acetonitrile; isopropyl alcohol / 3.5 h / 20 °C

8.1: acetic acid / tetrahydrofuran / 18 h / 20 °C

9.1: trifluoroacetic acid; pyridinium chlorochromate / acetonitrile / 3.5 h / 20 °C

10.1: potassium hexamethylsilazane / tetrahydrofuran; toluene / 1.43 h / -78 °C

11.1: bis(tri-n-butyltin); bis-triphenylphosphine-palladium(II) chloride / N,N-dimethyl-formamide / 0.25 h / 120 °C / Inert atmosphere

With pyridine; bis-triphenylphosphine-palladium(II) chloride; sodium hypochlorite; tetrapropylammonium perruthennate; trifluoromethylsulfonic anhydride; boron trifluoride diethyl etherate; bis(tri-n-butyltin); boron trichloride; potassium hexamethylsilazane; acetic acid; 4-methylmorpholine N-oxide; pyridinium chlorochromate; trifluoroacetic acid; zinc; In tetrahydrofuran; n-heptane; dichloromethane; di-isopropyl ether; water; N,N-dimethyl-formamide; isopropyl alcohol; toluene; acetonitrile;

Reference yield:

N-[(4aR,6R,8aS)-8a-(2,4-difluorophenyl)-6-(hydroxymethyl)-4,4-a,5,6,8,8a-hexahydropyrano[3,4-c][1,3]thiazin-2-yl]benzamide → N-[(4aR,8aS)-8a-(2,4-difluorophenyl)-6-(5-fluoro-1-methyl-1H-pyrazol-3-yl)-4,4a,8,8a-tetrahydropyrano[3,4-d][1,3]thiazin-2-yl]benzamide (1621585-56-5)

Guidance literature:

Multi-step reaction with 5 steps

1.1: triethylamine / dichloromethane / 0.08 h / 20 °C

1.2: 6.5 h / 20 °C

2.1: potassium carbonate / acetonitrile / 20.5 h / 20 °C / Inert atmosphere; Reflux

3.1: ruthenium trichloride; sodium periodate / water; acetonitrile; 1,2-dichloro-ethane / 21 h / 20 °C

4.1: potassium hexamethylsilazane / tetrahydrofuran; toluene / 1.43 h / -78 °C

5.1: bis(tri-n-butyltin); bis-triphenylphosphine-palladium(II) chloride / N,N-dimethyl-formamide / 0.25 h / 120 °C / Inert atmosphere

With ruthenium trichloride; bis-triphenylphosphine-palladium(II) chloride; sodium periodate; bis(tri-n-butyltin); potassium hexamethylsilazane; potassium carbonate; triethylamine; In tetrahydrofuran; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene; acetonitrile;

upstream raw materials:

5-fluoro-3-iodo-1-methyl-1H-pyrazole

(4aR,8aS)-2-(benzoylamino)-8a-(2,4-difluorophenyl)-4,4a,8,8a-tetrahydropyrano[3,4-d][1,3]thiazin-6-yl trifluoromethanesulfonate

(4aR,6S,8aS)-2-(benzoylamino)-8a-(2,4-difluorophenyl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-6-yl acetate

2-{[(2R)-1-(benzyloxy)pent-4-en-2-yl]oxy}-N-hydroxyethanimine

Downstream raw materials:

N-[(4aR,6R,8aS)-8a-(2,4-difluorophenyl)-6-(5-fluoro-1-methyl-1H-pyrazol-3-yl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-yl]benzamide

(4aR,6R,8aS)-8a-(2,4-difluorophenyl)-6-(5-fluoro-1-methyl-1H-pyrazol-3-yl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-amine