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

Base Information

Chemical Name: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
CAS No.:1622328-24-8
Molecular Formula:C₂₀H₁₇F₂N₃OS
Molecular Weight:385.437
Hs Code.:

Synonyms: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

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Chemical Property of 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

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Technology Process of 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

There total 17 articles about 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 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: 91.0%

: 1669434-23-4
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

: 1622328-24-8
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

Guidance literature:: With methanol; 1,8-diazabicyclo[5.4.0]undec-7-ene; at 80 ℃; for 16h;

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

: 1622328-24-8
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

Guidance literature:: Multi-step reaction with 8 steps

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

2: sulfur trioxide pyridine complex; dimethyl sulfoxide; triethylamine / dichloromethane / 6.5 h / 20 °C

3: potassium carbonate / acetonitrile / 2.5 h / Reflux; Inert atmosphere

4: sodium periodate; ruthenium trichloride / water; acetonitrile; 1,2-dichloro-ethane / 3 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

7: trifluoroacetic acid; triethylsilane / 1,2-dichloro-ethane / 16 h / 0 - 20 °C

8: 1,8-diazabicyclo[5.4.0]undec-7-ene; methanol / 16 h / 80 °C

With methanol; triethylsilane; ruthenium trichloride; bis-triphenylphosphine-palladium(II) chloride; sodium periodate; sulfur trioxide pyridine complex; boron trichloride; potassium hexamethylsilazane; potassium carbonate; caesium carbonate; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; trifluoroacetic acid; In tetrahydrofuran; n-heptane; dichloromethane; water; 1,2-dichloro-ethane; 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

: 1622328-24-8
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

Guidance literature:: Multi-step reaction with 7 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

6: trifluoroacetic acid; triethylsilane / 1,2-dichloro-ethane / 16 h / 0 - 20 °C

7: 1,8-diazabicyclo[5.4.0]undec-7-ene; methanol / 16 h / 80 °C

With methanol; triethylsilane; bis-triphenylphosphine-palladium(II) chloride; tetrapropylammonium permanganate; potassium hexamethylsilazane; caesium carbonate; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; pyridinium chlorochromate; trifluoroacetic acid; In tetrahydrofuran; water; acetic acid; 1,2-dichloro-ethane; toluene; acetonitrile; 5: |Suzuki Coupling;