4-{8-amino-3-[(6R,8aS)-1,1-dimethyl-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-[(6R,8aS)-1,1-dimethyl-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.: 1620675-47-9
• Molecular Formula: C₂₉H₂₈F₃N₇O₄
• Molecular Weight: 595.581
• Mol file: 1620675-47-9.mol

Synonyms:4-{8-amino-3-[(6R,8aS)-1,1-dimethyl-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-[(6R,8aS)-1,1-dimethyl-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-[(6R,8aS)-1,1-dimethyl-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 12 articles about 4-{8-amino-3-[(6R,8aS)-1,1-dimethyl-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: 72.0%

(6R,8aS)-6-(8-amino-1-bromoimidazo[1,5-a]pyrazin-3-yl)-1,1-dimethyltetrahydro-1H-oxazolo[3,4-a]pyridin-3(5H)-one (1620676-99-4) + 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-[(6R,8aS)-1,1-dimethyl-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 (1620675-47-9)

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate; In 1,4-dioxane; water; at 80 ℃; for 1h; Inert atmosphere;

Reference yield:

(3R,6S)-1-benzyl 3-methyl 6-(1-hydroxyethyl)piperidine-1,3-dicarboxylate (1620675-80-0) → 4-{8-amino-3-[(6R,8aS)-1,1-dimethyl-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 (1620675-47-9)

Guidance literature:

Multi-step reaction with 8 steps

1.1: Dess-Martin periodane / dichloromethane / 3 h / 0 - 25 °C

2.1: tetrahydrofuran; diethyl ether / 4 h / -78 - 0.25 °C

3.1: water; lithium hydroxide / tetrahydrofuran / 3 h / 25 °C

3.2: pH 1

4.1: N,N-dimethyl-formamide; oxalyl dichloride / dichloromethane / 1.5 h / 0 - 25 °C

4.2: 3 h / 25 °C

5.1: trichlorophosphate / acetonitrile / 15 h / 0 - 25 °C

6.1: N-Bromosuccinimide / acetonitrile / 2 h / 25 °C

7.1: ammonium hydroxide / isopropyl alcohol / 12 h / 100 °C / Sealed tube

8.1: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; 1,4-dioxane / 1 h / 80 °C / Inert atmosphere

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; ammonium hydroxide; N-Bromosuccinimide; oxalyl dichloride; water; potassium carbonate; Dess-Martin periodane; N,N-dimethyl-formamide; lithium hydroxide; trichlorophosphate; In tetrahydrofuran; 1,4-dioxane; diethyl ether; dichloromethane; water; isopropyl alcohol; acetonitrile;

Reference yield:

(3R,6S)-1-benzyl 3-methyl 6-(2-hydroxypropan-2-yl)piperidine-1,3-dicarboxylate (1620677-01-1) → 4-{8-amino-3-[(6R,8aS)-1,1-dimethyl-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 (1620675-47-9)

Guidance literature:

Multi-step reaction with 6 steps

1.1: water; lithium hydroxide / tetrahydrofuran / 3 h / 25 °C

1.2: pH 1

2.1: N,N-dimethyl-formamide; oxalyl dichloride / dichloromethane / 1.5 h / 0 - 25 °C

2.2: 3 h / 25 °C

3.1: trichlorophosphate / acetonitrile / 15 h / 0 - 25 °C

4.1: N-Bromosuccinimide / acetonitrile / 2 h / 25 °C

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

6.1: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; 1,4-dioxane / 1 h / 80 °C / Inert atmosphere

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

upstream raw materials:

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

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

(6R,8aS)-6-(8-amino-1-bromoimidazo[1,5-a]pyrazin-3-yl)-1,1-dimethyltetrahydro-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