N-[(4aR,7aR)-6-allyl-7a-(4-bromo-2-thienyl)-4,4a,5,7-tetrahydropyrrolo[3,4-d][1,3]thiazin-2-yl]benzamide

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Chemical Name:N-[(4aR,7aR)-6-allyl-7a-(4-bromo-2-thienyl)-4,4a,5,7-tetrahydropyrrolo[3,4-d][1,3]thiazin-2-yl]benzamide
CAS No.:1463486-18-1
Molecular Formula:C₂₀H₂₀BrN₃OS₂
Molecular Weight:462.434
Hs Code.:

Synonyms:N-[(4aR,7aR)-6-allyl-7a-(4-bromo-2-thienyl)-4,4a,5,7-tetrahydropyrrolo[3,4-d][1,3]thiazin-2-yl]benzamide

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

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

There total 8 articles about N-[(4aR,7aR)-6-allyl-7a-(4-bromo-2-thienyl)-4,4a,5,7-tetrahydropyrrolo[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:

: racemic N-[6-allyl-7a-(4-bromo-2-thienyl)-4,4a,5,7-tetrahydropyrrolo[3,4-d][1,3]thiazin-2-yl]benzamide

: 1463486-18-1
N-[(4aR,7aR)-6-allyl-7a-(4-bromo-2-thienyl)-4,4a,5,7-tetrahydropyrrolo[3,4-d][1,3]thiazin-2-yl]benzamide

: N-[(4aS,7aS)-6-allyl-7a-(4-bromo-2-thienyl)-4,4a,5,7-tetrahydropyrrolo[3,4-d][1,3]thiazin-2-yl]benzamide

Guidance literature:: With chiral HPLC: (Chiralpak AD; Resolution of racemate;

Reference yield:

: (±)-5-allyl-6a-(4-bromo-2-thienyl)-3,3a,4,6-tetrahydro-1Hpyrrolo[3,4-c]isoxazole

: 1463486-18-1
N-[(4aR,7aR)-6-allyl-7a-(4-bromo-2-thienyl)-4,4a,5,7-tetrahydropyrrolo[3,4-d][1,3]thiazin-2-yl]benzamide

: N-[(4aS,7aS)-6-allyl-7a-(4-bromo-2-thienyl)-4,4a,5,7-tetrahydropyrrolo[3,4-d][1,3]thiazin-2-yl]benzamide

Guidance literature:: Multi-step reaction with 4 steps

1.1: zinc; acetic acid / 4 h / 40 °C

2.1: N,O-Bis(trimethylsilyl)trifluoroacetamide / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere

2.2: 1 h / 20 °C / Inert atmosphere

3.1: 1-chloro-1-(dimethylamino)-2-methyl-1-propene / dichloromethane / 0 - 20 °C / Inert atmosphere

4.1: Chiralpak AD-H column / ethanol / Resolution of racemate

With 1-chloro-1-(dimethylamino)-2-methyl-1-propene; N,O-Bis(trimethylsilyl)trifluoroacetamide; acetic acid; zinc; In tetrahydrofuran; ethanol; dichloromethane;
DOI:10.1021/acs.jmedchem.1c00489

Reference yield:

: (±)-[1-allyl-4-amino-4-(4-bromo-2-thienyl)pyrrolidin-3-yl]methanol

: 1463486-18-1
N-[(4aR,7aR)-6-allyl-7a-(4-bromo-2-thienyl)-4,4a,5,7-tetrahydropyrrolo[3,4-d][1,3]thiazin-2-yl]benzamide

: N-[(4aS,7aS)-6-allyl-7a-(4-bromo-2-thienyl)-4,4a,5,7-tetrahydropyrrolo[3,4-d][1,3]thiazin-2-yl]benzamide

Guidance literature:: Multi-step reaction with 3 steps

1.1: N,O-Bis(trimethylsilyl)trifluoroacetamide / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere

1.2: 1 h / 20 °C / Inert atmosphere

2.1: 1-chloro-1-(dimethylamino)-2-methyl-1-propene / dichloromethane / 0 - 20 °C / Inert atmosphere

3.1: Chiralpak AD-H column / ethanol / Resolution of racemate

With 1-chloro-1-(dimethylamino)-2-methyl-1-propene; N,O-Bis(trimethylsilyl)trifluoroacetamide; In tetrahydrofuran; ethanol; dichloromethane;
DOI:10.1021/acs.jmedchem.1c00489