N-[(4aR,7aR)-7a-(2-thienyl)-4a,5,6,7-tetrahydro-4H-pyrrolo[3,4-d][1,3]thiazin-2-yl]benzamide

Base Information

Chemical Name:N-[(4aR,7aR)-7a-(2-thienyl)-4a,5,6,7-tetrahydro-4H-pyrrolo[3,4-d][1,3]thiazin-2-yl]benzamide
CAS No.:1463485-21-3
Molecular Formula:C₁₇H₁₇N₃OS₂
Molecular Weight:343.473
Hs Code.:

Synonyms:N-[(4aR,7aR)-7a-(2-thienyl)-4a,5,6,7-tetrahydro-4H-pyrrolo[3,4-d][1,3]thiazin-2-yl]benzamide

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Chemical Property of N-[(4aR,7aR)-7a-(2-thienyl)-4a,5,6,7-tetrahydro-4H-pyrrolo[3,4-d][1,3]thiazin-2-yl]benzamide

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Technology Process of N-[(4aR,7aR)-7a-(2-thienyl)-4a,5,6,7-tetrahydro-4H-pyrrolo[3,4-d][1,3]thiazin-2-yl]benzamide

There total 11 articles about N-[(4aR,7aR)-7a-(2-thienyl)-4a,5,6,7-tetrahydro-4H-pyrrolo[3,4-d][1,3]thiazin-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: 89.0%

: 1463486-24-9
benzyl (4aR,7aR)-2-benzamido-7a-(2-thienyl)-4,4a,5,7-tetrahydropyrrolo[3,4-d][1,3]thiazine-6-carboxylate

: 1463485-21-3
N-[(4aR,7aR)-7a-(2-thienyl)-4a,5,6,7-tetrahydro-4H-pyrrolo[3,4-d][1,3]thiazin-2-yl]benzamide

Guidance literature:: With trimethylsilyl iodide; In acetonitrile; at 20 ℃; Inert atmosphere;
DOI:10.1021/acs.jmedchem.1c00489

Reference yield:

: 1463484-39-0
benzyl 3,3a,4,6-tetrahydropyrrolo[3,4-c]isoxazole-5-carboxylate

: 1463485-21-3
N-[(4aR,7aR)-7a-(2-thienyl)-4a,5,6,7-tetrahydro-4H-pyrrolo[3,4-d][1,3]thiazin-2-yl]benzamide

Guidance literature:: Multi-step reaction with 6 steps

1.1: boron trifluoride diethyl etherate / tetrahydrofuran / 0.17 h / Inert atmosphere

1.2: 1 h / -78 °C

2.1: zinc; acetic acid / 2 h / 20 °C / Inert atmosphere

3.1: tetrahydrofuran / 2 h / 0 °C

4.1: 1-chloro-1-(dimethylamino)-2-methyl-1-propene / dichloromethane / 0 - 20 °C

5.1: SFC (Column: Chiralpak IC / methanol / Resolution of racemate

6.1: trimethylsilyl iodide / acetonitrile

With trimethylsilyl iodide; 1-chloro-1-(dimethylamino)-2-methyl-1-propene; boron trifluoride diethyl etherate; acetic acid; zinc; In tetrahydrofuran; methanol; dichloromethane; acetonitrile;

Reference yield:

: benzyl rel-(4aR,7aR)-2-benzamido-7a-(2-thienyl)-4,4a,5,7-tetrahydropyrrolo[3,4-d][1,3]thiazine-6-carboxylate

: 1463485-21-3
N-[(4aR,7aR)-7a-(2-thienyl)-4a,5,6,7-tetrahydro-4H-pyrrolo[3,4-d][1,3]thiazin-2-yl]benzamide

Guidance literature:: Multi-step reaction with 2 steps

1: SFC (Column: Chiralpak IC / methanol / Resolution of racemate

2: trimethylsilyl iodide / acetonitrile

With trimethylsilyl iodide; In methanol; acetonitrile;