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

Base Information

• Chemical Name: N-[(4aR,8aS)-6-(4-cyanophenyl)-8a-(2,4-difluorophenyl)-4,4a,8,8a-tetrahydropyrano[3,4-d][1,3]thiazin-2-yl]benzamide
• CAS No.: 1669433-79-7
• Molecular Formula: C₂₇H₁₉F₂N₃O₂S
• Molecular Weight: 487.53
• Mol file: 1669433-79-7.mol

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

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

There total 15 articles about N-[(4aR,8aS)-6-(4-cyanophenyl)-8a-(2,4-difluorophenyl)-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: 70.0%

(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) + 4-cyanophenylboronic acid (126747-14-6) → N-[(4aR,8aS)-6-(4-cyanophenyl)-8a-(2,4-difluorophenyl)-4,4a,8,8a-tetrahydropyrano[3,4-d][1,3]thiazin-2-yl]benzamide (1669433-79-7)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; caesium carbonate; In tetrahydrofuran; water; at 65 ℃; for 17h;

Reference yield:

N-[(4aR,6R,8aS)-6-[(benzyloxy)methyl]-8a-(2,4-difluorophenyl)-20 4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-yl]benzamide → N-[(4aR,8aS)-6-(4-cyanophenyl)-8a-(2,4-difluorophenyl)-4,4a,8,8a-tetrahydropyrano[3,4-d][1,3]thiazin-2-yl]benzamide (1669433-79-7)

Guidance literature:

Multi-step reaction with 6 steps

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

2: tetrapropylammonium permanganate; 4-methylmorpholine N-oxide / acetonitrile / 1.5 h / 20 °C

3: tetrahydrofuran; acetic acid / 18 h / 20 °C

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

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

6: caesium carbonate; bis-triphenylphosphine-palladium(II) chloride / tetrahydrofuran; water / 17 h / 65 °C

With bis-triphenylphosphine-palladium(II) chloride; tetrapropylammonium permanganate; boron trichloride; potassium hexamethylsilazane; caesium carbonate; 4-methylmorpholine N-oxide; pyridinium chlorochromate; trifluoroacetic acid; In tetrahydrofuran; n-heptane; dichloromethane; water; acetic acid; toluene; acetonitrile; 6: |Suzuki Coupling;

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)-6-(4-cyanophenyl)-8a-(2,4-difluorophenyl)-4,4a,8,8a-tetrahydropyrano[3,4-d][1,3]thiazin-2-yl]benzamide (1669433-79-7)

Guidance literature:

Multi-step reaction with 5 steps

1: tetrapropylammonium permanganate; 4-methylmorpholine N-oxide / acetonitrile / 1.5 h / 20 °C

2: tetrahydrofuran; acetic acid / 18 h / 20 °C

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

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

5: caesium carbonate; bis-triphenylphosphine-palladium(II) chloride / tetrahydrofuran; water / 17 h / 65 °C

With bis-triphenylphosphine-palladium(II) chloride; tetrapropylammonium permanganate; potassium hexamethylsilazane; caesium carbonate; 4-methylmorpholine N-oxide; pyridinium chlorochromate; trifluoroacetic acid; In tetrahydrofuran; water; acetic acid; toluene; acetonitrile; 5: |Suzuki Coupling;

upstream raw materials:

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

4-cyanophenylboronic acid

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

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

Downstream raw materials:

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

4-[(4aR,6R,8aS)-2-amino-8a-(2,4-difluorophenyl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-6-yl]benzonitrile