(S)-tert-butyl 1-(5-cyano-4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)ethylcarbamate

Base Information

Chemical Name:(S)-tert-butyl 1-(5-cyano-4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)ethylcarbamate
CAS No.:1403942-79-9
Molecular Formula:C₂₀H₂₁N₅O₃
Molecular Weight:379.418
Hs Code.:

Synonyms:(S)-tert-butyl 1-(5-cyano-4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)ethylcarbamate

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Chemical Property of (S)-tert-butyl 1-(5-cyano-4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)ethylcarbamate

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Technology Process of (S)-tert-butyl 1-(5-cyano-4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)ethylcarbamate

There total 8 articles about (S)-tert-butyl 1-(5-cyano-4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)ethylcarbamate 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: 57.0%

: 557-21-1
zinc(II) cyanide

: methyl (S)-tert-butyl 1-(5-bromo-4-oxo-3-phenyl-3,4-dihydropyrrolo[1,2-f][1,2,4]triazin-2-yl)ethylcarbamate

: 1403942-79-9
(S)-tert-butyl 1-(5-cyano-4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)ethylcarbamate

Guidance literature:: tetrakis(triphenylphosphine) palladium⁽⁰⁾; In N,N-dimethyl-formamide; at 120 ℃; sealed tube;

Reference yield: 57.0%

: 557-21-1
zinc(II) cyanide

: 1403942-70-0
(S)-tert-butyl 1-(5-bromo-4-oxo-3-phenyl-3,4-dihydropyrrolo[1,2-f][1,2,4]triazin-2-yl)ethylcarbamate

: 1403942-79-9
(S)-tert-butyl 1-(5-cyano-4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)ethylcarbamate

Guidance literature:: With tetrakis(triphenylphosphine) palladium⁽⁰⁾; In N,N-dimethyl-formamide; at 120 ℃; Sealed tube;
DOI:10.1021/acsmedchemlett.6b00438

Reference yield:

: 1192217-76-7
methyl 3-bromo-1-(phenylsulfonyl)-1H-pyrrole-2-carboxylate

: 1403942-79-9
(S)-tert-butyl 1-(5-cyano-4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)ethylcarbamate

Guidance literature:: Multi-step reaction with 6 steps

1.1: trimethylaluminum / toluene / 0.17 h / 20 °C / Inert atmosphere

1.2: 3 h / 80 °C

2.1: sodium hydroxide / methanol; water / 1.5 h / 20 °C

3.1: sodium hydroxide; ammonium hydroxide; ammonium chloride / water; diethyl ether; tert-butyl methyl ether / 0 °C

3.2: 1.83 h / 0 - 20 °C

4.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / tetrahydrofuran; dichloromethane / 55 °C

5.1: bromine; triphenylphosphine; triethylamine / dichloromethane / 3.5 h / 20 °C

5.2: 80 °C / Sealed tube

6.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / N,N-dimethyl-formamide / 120 °C / Sealed tube

With ammonium hydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; bromine; trimethylaluminum; ammonium chloride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; triphenylphosphine; sodium hydroxide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; tert-butyl methyl ether; water; N,N-dimethyl-formamide; toluene;
DOI:10.1021/acsmedchemlett.6b00438