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

Base Information

Chemical Name:N-[(4aR,7aR)-6-(5-fluoropyrimidin-2-yl)-7a-(2-thienyl)-4,4a,5,7-tetrahydropyrrolo[3,4-d][1,3]thiazin-2-yl]benzamide
CAS No.:1463485-31-5
Molecular Formula:C₂₁H₁₈FN₅OS₂
Molecular Weight:439.537
Hs Code.:

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

There total 13 articles about N-[(4aR,7aR)-6-(5-fluoropyrimidin-2-yl)-7a-(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: 98.0%

: 1463485-09-7
N-[(4aR,7aR)-7a-(2-thienyl)-4a,5,6,7-tetrahydro-4H-pyrrolo[3,4-d][1,3]thiazin-2-yl]benzamide hydrochloride

: 62802-42-0
2-chloro-5-fluoropyrimidine

: 1463485-31-5
N-[(4aR,7aR)-6-(5-fluoropyrimidin-2-yl)-7a-(2-thienyl)-4,4a,5,7-tetrahydropyrrolo[3,4-d][1,3]thiazin-2-yl]benzamide

Guidance literature:: With triethylamine; at 110 ℃; for 4h;

Reference yield: 71.0%

: 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

: 62802-42-0
2-chloro-5-fluoropyrimidine

: 1463485-31-5
N-[(4aR,7aR)-6-(5-fluoropyrimidin-2-yl)-7a-(2-thienyl)-4,4a,5,7-tetrahydropyrrolo[3,4-d][1,3]thiazin-2-yl]benzamide

Guidance literature:: With N,N,N',N'-tetramethylguanidine; In dimethyl sulfoxide; at 50 ℃; for 4h;

Reference yield:

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

: 1463485-31-5
N-[(4aR,7aR)-6-(5-fluoropyrimidin-2-yl)-7a-(2-thienyl)-4,4a,5,7-tetrahydropyrrolo[3,4-d][1,3]thiazin-2-yl]benzamide

Guidance literature:: Multi-step reaction with 7 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

7.1: N,N,N',N'-tetramethylguanidine / dimethyl sulfoxide / 4 h / 50 °C

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