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}-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}-N-[4-(trifluoromethyl)pyridin-2-yl]benzamide
• CAS No.: 1620673-70-2
• Molecular Formula: C₂₈H₂₆F₃N₇O₃
• Molecular Weight: 565.555
• Mol file: 1620673-70-2.mol

Synonyms:

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}-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}-N-[4-(trifluoromethyl)pyridin-2-yl]benzamide

There total 16 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}-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:

5-(methoxycarbonyl)-2-methylpyridine 1-oxide (49668-89-5) → 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}-N-[4-(trifluoromethyl)pyridin-2-yl]benzamide (1620673-70-2)

Guidance literature:

Multi-step reaction with 14 steps

1: 1 h / 130 °C

2: sodium cyanoborohydride / acetic acid / 24 h / 20 °C

3: sodium hydrogencarbonate / 24 h / 0 - 20 °C

4: hydrogenchloride / methanol / 24 h / Reflux

5: Dess-Martin periodane / dichloromethane / 20 °C

6: tetrahydrofuran / -78 °C

7: Dess-Martin periodane / dichloromethane / 20 °C

8: tetrahydrofuran / 4 h / -78 - -25 °C

9: lithium hydroxide; water / tetrahydrofuran / 3 h

10: isopropyl chloroformate; triethylamine / 3 h

11: trichlorophosphate / acetonitrile / 15 h / 20 °C

12: N-Bromosuccinimide / N,N-dimethyl-formamide / 1 h / 20 °C

13: isopropyl alcohol / 7 h / 100 °C / Sealed tube

14: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / 1,4-dioxane / 2 h / 100 °C

With hydrogenchloride; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; N-Bromosuccinimide; water; sodium cyanoborohydride; sodium hydrogencarbonate; potassium carbonate; Dess-Martin periodane; isopropyl chloroformate; triethylamine; lithium hydroxide; trichlorophosphate; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; acetic acid; N,N-dimethyl-formamide; isopropyl alcohol; acetonitrile; 14: |Suzuki Coupling;

DOI:10.1016/j.bmcl.2020.127390

Reference yield:

C18H23NO6 → 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}-N-[4-(trifluoromethyl)pyridin-2-yl]benzamide (1620673-70-2)

Guidance literature:

Multi-step reaction with 11 steps

1: hydrogenchloride / methanol / 24 h / Reflux

2: Dess-Martin periodane / dichloromethane / 20 °C

3: tetrahydrofuran / -78 °C

4: Dess-Martin periodane / dichloromethane / 20 °C

5: tetrahydrofuran / 4 h / -78 - -25 °C

6: lithium hydroxide; water / tetrahydrofuran / 3 h

7: isopropyl chloroformate; triethylamine / 3 h

8: trichlorophosphate / acetonitrile / 15 h / 20 °C

9: N-Bromosuccinimide / N,N-dimethyl-formamide / 1 h / 20 °C

10: isopropyl alcohol / 7 h / 100 °C / Sealed tube

11: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / 1,4-dioxane / 2 h / 100 °C

With hydrogenchloride; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; N-Bromosuccinimide; water; potassium carbonate; Dess-Martin periodane; isopropyl chloroformate; triethylamine; lithium hydroxide; trichlorophosphate; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; N,N-dimethyl-formamide; isopropyl alcohol; acetonitrile; 11: |Suzuki Coupling;

DOI:10.1016/j.bmcl.2020.127390

Reference yield:

Methyl 6-methylnicotinate (5470-70-2) → 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}-N-[4-(trifluoromethyl)pyridin-2-yl]benzamide (1620673-70-2)

Guidance literature:

Multi-step reaction with 15 steps

1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 20 °C

2: 1 h / 130 °C

3: sodium cyanoborohydride / acetic acid / 24 h / 20 °C

4: sodium hydrogencarbonate / 24 h / 0 - 20 °C

5: hydrogenchloride / methanol / 24 h / Reflux

6: Dess-Martin periodane / dichloromethane / 20 °C

7: tetrahydrofuran / -78 °C

8: Dess-Martin periodane / dichloromethane / 20 °C

9: tetrahydrofuran / 4 h / -78 - -25 °C

10: lithium hydroxide; water / tetrahydrofuran / 3 h

11: isopropyl chloroformate; triethylamine / 3 h

12: trichlorophosphate / acetonitrile / 15 h / 20 °C

13: N-Bromosuccinimide / N,N-dimethyl-formamide / 1 h / 20 °C

14: isopropyl alcohol / 7 h / 100 °C / Sealed tube

15: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / 1,4-dioxane / 2 h / 100 °C

With hydrogenchloride; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; N-Bromosuccinimide; water; sodium cyanoborohydride; sodium hydrogencarbonate; potassium carbonate; Dess-Martin periodane; isopropyl chloroformate; triethylamine; 3-chloro-benzenecarboperoxoic acid; lithium hydroxide; trichlorophosphate; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; acetic acid; N,N-dimethyl-formamide; isopropyl alcohol; acetonitrile; 15: |Suzuki Coupling;

DOI:10.1016/j.bmcl.2020.127390

upstream raw materials:

Methyl 6-methylnicotinate

5-(methoxycarbonyl)-2-methylpyridine 1-oxide

methyl 6-(acetoxymethyl)nicotinate

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