4-{8-amino-3-[(1R,6R,8aS)-1-methyl-3-oxohexahydro[1,3]oxazolo[3,4-a]pyridin-6-yl]imidazo[1,5-a]pyrazin-1-yl}-3-methoxy-N-[4-(trifluoromethyl)pyridin-2-yl]benzamide

Base Information

• Chemical Name: 4-{8-amino-3-[(1R,6R,8aS)-1-methyl-3-oxohexahydro[1,3]oxazolo[3,4-a]pyridin-6-yl]imidazo[1,5-a]pyrazin-1-yl}-3-methoxy-N-[4-(trifluoromethyl)pyridin-2-yl]benzamide
• CAS No.: 1620674-09-0
• Molecular Formula: C₂₈H₂₆F₃N₇O₄
• Molecular Weight: 581.554
• Mol file: 1620674-09-0.mol

Synonyms:4-{8-amino-3-[(1R,6R,8aS)-1-methyl-3-oxohexahydro[1,3]oxazolo[3,4-a]pyridin-6-yl]imidazo[1,5-a]pyrazin-1-yl}-3-methoxy-N-[4-(trifluoromethyl)pyridin-2-yl]benzamide

Chemical Property of 4-{8-amino-3-[(1R,6R,8aS)-1-methyl-3-oxohexahydro[1,3]oxazolo[3,4-a]pyridin-6-yl]imidazo[1,5-a]pyrazin-1-yl}-3-methoxy-N-[4-(trifluoromethyl)pyridin-2-yl]benzamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-{8-amino-3-[(1R,6R,8aS)-1-methyl-3-oxohexahydro[1,3]oxazolo[3,4-a]pyridin-6-yl]imidazo[1,5-a]pyrazin-1-yl}-3-methoxy-N-[4-(trifluoromethyl)pyridin-2-yl]benzamide

There total 11 articles about 4-{8-amino-3-[(1R,6R,8aS)-1-methyl-3-oxohexahydro[1,3]oxazolo[3,4-a]pyridin-6-yl]imidazo[1,5-a]pyrazin-1-yl}-3-methoxy-N-[4-(trifluoromethyl)pyridin-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:

(1R,6R,8aS)-6-(8-amino-1-bromo-imidazo[1,5-a]pyrazin-3-yl)-1-methyltetrahydro-1H-oxazolo[3,4-a]pyridin-3(5H)-one (1620675-87-7) + 3-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-N-(4-(trifluoromethyl)pyridin-2-yl)benzamide (1419221-70-7) → 4-{8-amino-3-[(1R,6R,8aS)-1-methyl-3-oxohexahydro[1,3]oxazolo[3,4-a]pyridin-6-yl]imidazo[1,5-a]pyrazin-1-yl}-3-methoxy-N-[4-(trifluoromethyl)pyridin-2-yl]benzamide (1620674-09-0)

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate; In 1,4-dioxane; water; at 90 - 100 ℃; for 1h; Inert atmosphere;

Reference yield:

(3R,6S)-1-benzyl 3-methyl 6-formylpiperidine-1,3-dicarboxylate (1620675-81-1) → 4-{8-amino-3-[(1R,6R,8aS)-1-methyl-3-oxohexahydro[1,3]oxazolo[3,4-a]pyridin-6-yl]imidazo[1,5-a]pyrazin-1-yl}-3-methoxy-N-[4-(trifluoromethyl)pyridin-2-yl]benzamide (1620674-09-0)

Guidance literature:

Multi-step reaction with 8 steps

1.1: tetrahydrofuran / 2 h / -78 °C

2.1: lithium hydroxide monohydrate; water / tetrahydrofuran / 12 h / 25 °C / Inert atmosphere

2.2: pH 5-6

3.1: N,N-dimethyl-formamide; oxalyl dichloride / dichloromethane / 2 h / 5 - 30 °C

3.2: 12 h / 30 °C

4.1: trichlorophosphate; N,N-dimethyl-formamide / acetonitrile / 12 h / 25 °C / Cooling with ice

5.1: N-Bromosuccinimide / N,N-dimethyl-formamide / 2 h

6.1: ammonium hydroxide / isopropyl alcohol / 12 h / 100 °C

7.1: AS column / methanol; carbon dioxide / 38 °C / Resolution of racemate; liquid CO₂

8.1: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; 1,4-dioxane / 1 h / 90 - 100 °C / Inert atmosphere

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; ammonium hydroxide; N-Bromosuccinimide; oxalyl dichloride; lithium hydroxide monohydrate; water; potassium carbonate; N,N-dimethyl-formamide; trichlorophosphate; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; carbon dioxide; water; N,N-dimethyl-formamide; isopropyl alcohol; acetonitrile;

Reference yield:

(3R,6S)-1-benzyl 3-methyl 6-(1-hydroxyethyl)piperidine-1,3-dicarboxylate (1620675-80-0) → 4-{8-amino-3-[(1R,6R,8aS)-1-methyl-3-oxohexahydro[1,3]oxazolo[3,4-a]pyridin-6-yl]imidazo[1,5-a]pyrazin-1-yl}-3-methoxy-N-[4-(trifluoromethyl)pyridin-2-yl]benzamide (1620674-09-0)

Guidance literature:

Multi-step reaction with 7 steps

1.1: lithium hydroxide monohydrate; water / tetrahydrofuran / 12 h / 25 °C / Inert atmosphere

1.2: pH 5-6

2.1: N,N-dimethyl-formamide; oxalyl dichloride / dichloromethane / 2 h / 5 - 30 °C

2.2: 12 h / 30 °C

3.1: trichlorophosphate; N,N-dimethyl-formamide / acetonitrile / 12 h / 25 °C / Cooling with ice

4.1: N-Bromosuccinimide / N,N-dimethyl-formamide / 2 h

5.1: ammonium hydroxide / isopropyl alcohol / 12 h / 100 °C

6.1: AS column / methanol; carbon dioxide / 38 °C / Resolution of racemate; liquid CO₂

7.1: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; 1,4-dioxane / 1 h / 90 - 100 °C / Inert atmosphere

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; ammonium hydroxide; N-Bromosuccinimide; oxalyl dichloride; lithium hydroxide monohydrate; water; potassium carbonate; N,N-dimethyl-formamide; trichlorophosphate; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; carbon dioxide; water; N,N-dimethyl-formamide; isopropyl alcohol; acetonitrile;

upstream raw materials:

(1R,6R,8aS)-6-(8-amino-1-bromo-imidazo[1,5-a]pyrazin-3-yl)-1-methyltetrahydro-1H-oxazolo[3,4-a]pyridin-3(5H)-one

3-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-N-(4-(trifluoromethyl)pyridin-2-yl)benzamide

3-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoyl chloride

(3R,6S)-1-benzyl 3-methyl 6-formylpiperidine-1,3-dicarboxylate