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}-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}-N-[4-(trifluoromethyl)pyridin-2-yl]benzamide
CAS No.:1620673-64-4
Molecular Formula:C₂₇H₂₄F₃N₇O₃
Molecular Weight:551.528
Hs Code.:

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

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

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

There total 14 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}-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:

: 1418307-30-8
4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-N-(4-trifluoromethyl-pyridin-2-yl)-benzamide

: 1620675-86-6
(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

: 1620673-62-2
4-{8-amino-3-[(1S,6R,8aS)-1-methyl-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

: 1620673-64-4
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}-N-[4-(trifluoromethyl)pyridin-2-yl]benzamide

Guidance literature:: With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate; In 1,4-dioxane; at 100 ℃; for 2h;
DOI:10.1016/j.bmcl.2020.127390

Reference yield:

: 49668-89-5
5-(methoxycarbonyl)-2-methylpyridine 1-oxide

: 1620673-62-2
4-{8-amino-3-[(1S,6R,8aS)-1-methyl-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

: 1620673-64-4
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}-N-[4-(trifluoromethyl)pyridin-2-yl]benzamide

Guidance literature:: Multi-step reaction with 12 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: lithium hydroxide; water / tetrahydrofuran / 12 h / 20 °C

8: isopropyl chloroformate; triethylamine / 3 h

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

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

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

12: (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; 12: |Suzuki Coupling;
DOI:10.1016/j.bmcl.2020.127390

Reference yield:

: 63362-34-5
methyl 6-(acetoxymethyl)nicotinate

: 1620673-62-2
4-{8-amino-3-[(1S,6R,8aS)-1-methyl-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

: 1620673-64-4
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}-N-[4-(trifluoromethyl)pyridin-2-yl]benzamide

Guidance literature:: Multi-step reaction with 11 steps

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

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

3: hydrogenchloride / methanol / 24 h / Reflux

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

5: tetrahydrofuran / -78 °C

6: lithium hydroxide; water / tetrahydrofuran / 12 h / 20 °C

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; 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; 11: |Suzuki Coupling;
DOI:10.1016/j.bmcl.2020.127390