N-(3-((6-cyano-2-oxo-1,2-dihydroquinolin-3-yl)amino)phenyl)pyrrolidine-1-carboxamide

Base Information

Chemical Name:N-(3-((6-cyano-2-oxo-1,2-dihydroquinolin-3-yl)amino)phenyl)pyrrolidine-1-carboxamide
CAS No.:1616393-32-8
Molecular Formula:C₂₁H₁₉N₅O₂
Molecular Weight:373.414
Hs Code.:

Synonyms:N-(3-((6-cyano-2-oxo-1,2-dihydroquinolin-3-yl)amino)phenyl)pyrrolidine-1-carboxamide

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Chemical Property of N-(3-((6-cyano-2-oxo-1,2-dihydroquinolin-3-yl)amino)phenyl)pyrrolidine-1-carboxamide

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Technology Process of N-(3-((6-cyano-2-oxo-1,2-dihydroquinolin-3-yl)amino)phenyl)pyrrolidine-1-carboxamide

There total 8 articles about N-(3-((6-cyano-2-oxo-1,2-dihydroquinolin-3-yl)amino)phenyl)pyrrolidine-1-carboxamide 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: 29.0%

: 1616393-16-8
N-(3-((6-cyano-1-(4-methoxybenzyl)-2-oxo-1,2-dihydroquinolin-3-yl)amino)phenyl)pyrrolidine-1-carboxamide

: 1616393-32-8
N-(3-((6-cyano-2-oxo-1,2-dihydroquinolin-3-yl)amino)phenyl)pyrrolidine-1-carboxamide

Guidance literature:: With trifluorormethanesulfonic acid; trifluoroacetic acid; at 20 ℃; for 3h;
DOI:10.1016/j.bmc.2014.04.037

Reference yield:

: 64495-55-2
6-nitro-1,2-dihydroquinolin-2-one

: 1616393-32-8
N-(3-((6-cyano-2-oxo-1,2-dihydroquinolin-3-yl)amino)phenyl)pyrrolidine-1-carboxamide

Guidance literature:: Multi-step reaction with 7 steps

1.1: sodium bromate; hydrogen bromide / water / 4 h / 100 °C

2.1: potassium carbonate / N,N-dimethyl-formamide / 20 - 50 °C

3.1: acetic acid; zinc / methanol / 0.5 h

4.1: hydrogenchloride; sodium nitrite / water / 1.08 h / -5 °C

4.2: -5 - 20 °C

5.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 4 h / 90 °C / Inert atmosphere

6.1: XPhos; potassium carbonate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾ / tert-butyl alcohol / Reflux; Inert atmosphere

7.1: trifluoroacetic acid; trifluorormethanesulfonic acid / 3 h / 20 °C

With hydrogenchloride; sodium bromate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tetrakis(triphenylphosphine) palladium⁽⁰⁾; trifluorormethanesulfonic acid; hydrogen bromide; potassium carbonate; acetic acid; trifluoroacetic acid; zinc; sodium nitrite; XPhos; In methanol; water; N,N-dimethyl-formamide; tert-butyl alcohol; 6.1: |Buchwald-Hartwig Coupling;
DOI:10.1016/j.bmc.2014.04.037

Reference yield:

: 296759-30-3
3-bromo-6-nitro-1,2-dihydroquinolin-2-one

: 1616393-32-8
N-(3-((6-cyano-2-oxo-1,2-dihydroquinolin-3-yl)amino)phenyl)pyrrolidine-1-carboxamide

Guidance literature:: Multi-step reaction with 6 steps

1.1: potassium carbonate / N,N-dimethyl-formamide / 20 - 50 °C

2.1: acetic acid; zinc / methanol / 0.5 h

3.1: hydrogenchloride; sodium nitrite / water / 1.08 h / -5 °C

3.2: -5 - 20 °C

4.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 4 h / 90 °C / Inert atmosphere

5.1: XPhos; potassium carbonate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾ / tert-butyl alcohol / Reflux; Inert atmosphere

6.1: trifluoroacetic acid; trifluorormethanesulfonic acid / 3 h / 20 °C

With hydrogenchloride; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tetrakis(triphenylphosphine) palladium⁽⁰⁾; trifluorormethanesulfonic acid; potassium carbonate; acetic acid; trifluoroacetic acid; zinc; sodium nitrite; XPhos; In methanol; water; N,N-dimethyl-formamide; tert-butyl alcohol; 5.1: |Buchwald-Hartwig Coupling;
DOI:10.1016/j.bmc.2014.04.037