(E,E)-4-[[3-(1-dimethylsulfamoyl-1H-imidazol-4-yl)-2-propenyl]benzylamino]-4-oxo-2-butenoic acid ethyl ester

Base Information

Chemical Name:(E,E)-4-[[3-(1-dimethylsulfamoyl-1H-imidazol-4-yl)-2-propenyl]benzylamino]-4-oxo-2-butenoic acid ethyl ester
CAS No.:610768-48-4
Molecular Formula:C₂₁H₂₆N₄O₅S
Molecular Weight:446.527
Hs Code.:

Synonyms:(E,E)-4-[[3-(1-dimethylsulfamoyl-1H-imidazol-4-yl)-2-propenyl]benzylamino]-4-oxo-2-butenoic acid ethyl ester

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Chemical Property of (E,E)-4-[[3-(1-dimethylsulfamoyl-1H-imidazol-4-yl)-2-propenyl]benzylamino]-4-oxo-2-butenoic acid ethyl ester

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Technology Process of (E,E)-4-[[3-(1-dimethylsulfamoyl-1H-imidazol-4-yl)-2-propenyl]benzylamino]-4-oxo-2-butenoic acid ethyl ester

There total 15 articles about (E,E)-4-[[3-(1-dimethylsulfamoyl-1H-imidazol-4-yl)-2-propenyl]benzylamino]-4-oxo-2-butenoic acid ethyl ester 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%

: 26367-48-6
fumaric acid ethyl ester mono chloride

: 610768-37-1
N-benzyl-N-[(2E)-3-(1-dimethylsulfamoyl-1H-imidazol-4-yl)-2-propenyl]amine

: 610768-48-4
(E,E)-4-[[3-(1-dimethylsulfamoyl-1H-imidazol-4-yl)-2-propenyl]benzylamino]-4-oxo-2-butenoic acid ethyl ester

: (+/-)-(3aS,4S,4aR,7aS)-3-dimethylsulfamoyl-3a,4a,5,6,7,7a-hexahydro-5-oxo-6-benzyl-5H-imidazo[4,5-f]isoindole-4-carboxylic acid ethyl ester

Guidance literature:: With sodium hydrogencarbonate; In dichloromethane; at 0 - 20 ℃;
DOI:10.1021/ol0352862

Reference yield:

: 223571-74-2
methyl (E)-3-(1-(N,N-dimethylsulfamoyl)-1H-imidazol-4-yl)acrylate

: 610768-48-4
(E,E)-4-[[3-(1-dimethylsulfamoyl-1H-imidazol-4-yl)-2-propenyl]benzylamino]-4-oxo-2-butenoic acid ethyl ester

Guidance literature:: Multi-step reaction with 6 steps

1.1: 86 percent / DIBAL-H / CH₂Cl₂; hexane / -78 - 20 °C

2.1: 100 percent / SOCl₂ / CH₂Cl₂ / 2 h / 20 °C

3.1: 100 percent / dimethylformamide / 20 °C

4.1: 90 percent / hydrazine monohydrate / ethanol / 3 h / Heating

5.1: ethanol / 2 h / 20 °C

5.2: 92 percent / NaBH₄ / ethanol / 20 °C

6.1: 92 percent / NaHCO₃ / CH₂Cl₂ / 0 - 20 °C

With thionyl chloride; diisobutylaluminium hydride; sodium hydrogencarbonate; hydrazine hydrate; In ethanol; hexane; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ol0352862

Reference yield:

: 70346-51-9
(E)-methyl 3-(1H-imidazol-4-yl)acrylate

: 610768-48-4
(E,E)-4-[[3-(1-dimethylsulfamoyl-1H-imidazol-4-yl)-2-propenyl]benzylamino]-4-oxo-2-butenoic acid ethyl ester

Guidance literature:: Multi-step reaction with 7 steps

1.1: NaH / tetrahydrofuran / 1.5 h / 0 - 20 °C

1.2: 92 percent / tetrahydrofuran / 0 - 20 °C

2.1: 86 percent / DIBAL-H / CH₂Cl₂; hexane / -78 - 20 °C

3.1: 100 percent / SOCl₂ / CH₂Cl₂ / 2 h / 20 °C

4.1: 100 percent / dimethylformamide / 20 °C

5.1: 90 percent / hydrazine monohydrate / ethanol / 3 h / Heating

6.1: ethanol / 2 h / 20 °C

6.2: 92 percent / NaBH₄ / ethanol / 20 °C

7.1: 92 percent / NaHCO₃ / CH₂Cl₂ / 0 - 20 °C

With thionyl chloride; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; hydrazine hydrate; In tetrahydrofuran; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ol0352862