1-benzyl-3-(7-hydroxy-1,1-dioxo-1,4-dihydro-1λ⁶-benzo[1,2,4]thiadiazin-3-yl)-4-hydroxy-5-(pyridin-2-yl)-1,5-dihydropyrrol-2-one

Base Information

• Chemical Name: 1-benzyl-3-(7-hydroxy-1,1-dioxo-1,4-dihydro-1λ⁶-benzo[1,2,4]thiadiazin-3-yl)-4-hydroxy-5-(pyridin-2-yl)-1,5-dihydropyrrol-2-one
• CAS No.: 630133-04-9
• Molecular Formula: C₂₃H₁₈N₄O₅S
• Molecular Weight: 462.486

Synonyms:1-benzyl-3-(7-hydroxy-1,1-dioxo-1,4-dihydro-1λ⁶-benzo[1,2,4]thiadiazin-3-yl)-4-hydroxy-5-(pyridin-2-yl)-1,5-dihydropyrrol-2-one

Chemical Property of 1-benzyl-3-(7-hydroxy-1,1-dioxo-1,4-dihydro-1λ⁶-benzo[1,2,4]thiadiazin-3-yl)-4-hydroxy-5-(pyridin-2-yl)-1,5-dihydropyrrol-2-one

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Technology Process of 1-benzyl-3-(7-hydroxy-1,1-dioxo-1,4-dihydro-1λ⁶-benzo[1,2,4]thiadiazin-3-yl)-4-hydroxy-5-(pyridin-2-yl)-1,5-dihydropyrrol-2-one

There total 4 articles about 1-benzyl-3-(7-hydroxy-1,1-dioxo-1,4-dihydro-1λ⁶-benzo[1,2,4]thiadiazin-3-yl)-4-hydroxy-5-(pyridin-2-yl)-1,5-dihydropyrrol-2-one 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: 92.0%

methyl 2-(benzylamino)-2-(pyridin-2-yl)acetate (630132-97-7) + (7-hydroxy-1,1-dioxo-1,4-dihydro-1λ6-benzo[1,2,4]thiadiazin-3-yl)-acetic acid (872359-12-1) → 1-benzyl-3-(7-hydroxy-1,1-dioxo-1,4-dihydro-1λ6-benzo[1,2,4]thiadiazin-3-yl)-4-hydroxy-5-(pyridin-2-yl)-1,5-dihydropyrrol-2-one (630133-04-9)

Guidance literature:

methyl 2-(benzylamino)-2-(pyridin-2-yl)acetate; (7-hydroxy-1,1-dioxo-1,4-dihydro-1λ6-benzo[1,2,4]thiadiazin-3-yl)-acetic acid; With dicyclohexyl-carbodiimide; In dichloromethane; N,N-dimethyl-formamide; at 20 ℃;

With triethylamine; In dichloromethane; N,N-dimethyl-formamide; at 20 ℃;

DOI:10.1021/ol052371w

Reference yield:

methyl 2-bromo-2-(pyridin-2-yl) acetate (52458-81-8) → 1-benzyl-3-(7-hydroxy-1,1-dioxo-1,4-dihydro-1λ6-benzo[1,2,4]thiadiazin-3-yl)-4-hydroxy-5-(pyridin-2-yl)-1,5-dihydropyrrol-2-one (630133-04-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 56 percent / potassium carbonate / tetrahydrofuran / 16 h / 20 °C

2.1: dicyclohexylcarbodiimide / CH₂Cl₂; dimethylformamide / 20 °C

2.2: 92 percent / triethylamine / CH₂Cl₂; dimethylformamide / 20 °C

With potassium carbonate; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 2.2: Dieckmann cyclization;

DOI:10.1021/ol052371w

Reference yield:

benzylamine (100-46-9) → 1-benzyl-3-(7-hydroxy-1,1-dioxo-1,4-dihydro-1λ6-benzo[1,2,4]thiadiazin-3-yl)-4-hydroxy-5-(pyridin-2-yl)-1,5-dihydropyrrol-2-one (630133-04-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 56 percent / potassium carbonate / tetrahydrofuran / 16 h / 20 °C

2.1: dicyclohexylcarbodiimide / CH₂Cl₂; dimethylformamide / 20 °C

2.2: 92 percent / triethylamine / CH₂Cl₂; dimethylformamide / 20 °C

With potassium carbonate; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 2.2: Dieckmann cyclization;

DOI:10.1021/ol052371w

upstream raw materials:

methyl 2-(benzylamino)-2-(pyridin-2-yl)acetate

(7-hydroxy-1,1-dioxo-1,4-dihydro-1λ6-benzo[1,2,4]thiadiazin-3-yl)-acetic acid

methyl 2-bromo-2-(pyridin-2-yl) acetate

benzylamine

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