N-[4-[6-[1-(Difluoromethyl)cyclopropyl]-8-(2,4-dioxopyrimidin-1-yl)-5-methoxy-3-quinolyl]phenyl]methanesulfonamide

Base Information

Chemical Name:N-[4-[6-[1-(Difluoromethyl)cyclopropyl]-8-(2,4-dioxopyrimidin-1-yl)-5-methoxy-3-quinolyl]phenyl]methanesulfonamide
CAS No.:1257833-31-0
Molecular Formula:C₂₅H₂₂F₂N₄O₅S
Molecular Weight:528.536
Hs Code.:

Synonyms:N-[4-[6-[1-(Difluoromethyl)cyclopropyl]-8-(2,4-dioxopyrimidin-1-yl)-5-methoxy-3-quinolyl]phenyl]methanesulfonamide

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Chemical Property of N-[4-[6-[1-(Difluoromethyl)cyclopropyl]-8-(2,4-dioxopyrimidin-1-yl)-5-methoxy-3-quinolyl]phenyl]methanesulfonamide

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Technology Process of N-[4-[6-[1-(Difluoromethyl)cyclopropyl]-8-(2,4-dioxopyrimidin-1-yl)-5-methoxy-3-quinolyl]phenyl]methanesulfonamide

There total 12 articles about N-[4-[6-[1-(Difluoromethyl)cyclopropyl]-8-(2,4-dioxopyrimidin-1-yl)-5-methoxy-3-quinolyl]phenyl]methanesulfonamide 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: 93.0%

: 1485749-42-5
N-[4-[8-amino-6-[1-(difluoromethyl)cyclopropyl]-5-methoxy-3-quinolyl]phenyl]methanesulfonamide

: 3315-16-0
silver cyanate

: 6192-00-3,60778-73-6
(2E)-3-methoxy-2-propenoyl chloride

: 1257833-31-0
N-[4-[6-[1-(Difluoromethyl)cyclopropyl]-8-(2,4-dioxopyrimidin-1-yl)-5-methoxy-3-quinolyl]phenyl]methanesulfonamide

Guidance literature:: silver cyanate; (2E)-3-methoxy-2-propenoyl chloride; In toluene; at 130 ℃; for 0.5h; Inert atmosphere;

N-[4-[8-amino-6-[1-(difluoromethyl)cyclopropyl]-5-methoxy-3-quinolyl]phenyl]methanesulfonamide; In N,N-dimethyl-formamide; toluene; at 0 ℃; for 0.75h; Inert atmosphere;

With sulfuric acid; In ethanol; water; at 110 ℃; for 1.5h; Inert atmosphere;
DOI:10.1021/jm401329s

Reference yield:

: 111049-68-4
methyl 4-amino-5-bromo-2-methoxybenzenecarboxylate

: 1257833-31-0
N-[4-[6-[1-(Difluoromethyl)cyclopropyl]-8-(2,4-dioxopyrimidin-1-yl)-5-methoxy-3-quinolyl]phenyl]methanesulfonamide

Guidance literature:: Multi-step reaction with 11 steps

1.1: bromine; acetic acid / 0.25 h / 100 °C / Inert atmosphere

2.1: diisobutylaluminium hydride / dichloromethane / 0 °C / Inert atmosphere

3.1: carbon tetrabromide; triphenylphosphine / dichloromethane / 19 h / 20 °C / Inert atmosphere

4.1: dichloromethane; water / 0.25 h / Inert atmosphere; Reflux

5.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / 20 °C / Inert atmosphere

6.1: diisobutylaluminium hydride / dichloromethane / 1 h / -78 °C / Inert atmosphere

6.2: Inert atmosphere

7.1: diethylamino-sulfur trifluoride / dichloromethane / 72 h / 20 °C / Inert atmosphere

8.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / methanol; toluene / 1 h / 120 °C / Inert atmosphere; Microwave irradiation

9.1: tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; tert-butyl XPhos; sodium t-butanolate / toluene / 72 h / 20 °C / Inert atmosphere

10.1: hydrogenchloride / dichloromethane; 1,4-dioxane / 1 h / 20 °C / Inert atmosphere

11.1: toluene / 0.5 h / 130 °C / Inert atmosphere

11.2: 0.75 h / 0 °C / Inert atmosphere

11.3: 1.5 h / 110 °C / Inert atmosphere

With hydrogenchloride; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; tetrakis(triphenylphosphine) palladium⁽⁰⁾; carbon tetrabromide; diethylamino-sulfur trifluoride; bromine; sodium hydride; diisobutylaluminium hydride; sodium carbonate; acetic acid; triphenylphosphine; sodium t-butanolate; tert-butyl XPhos; In 1,4-dioxane; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; mineral oil;
DOI:10.1021/jm401329s

Reference yield:

: 1257833-16-1
methyl 3,8-dibromo-5-methoxyquinoline-6-carboxylate

: 1257833-31-0
N-[4-[6-[1-(Difluoromethyl)cyclopropyl]-8-(2,4-dioxopyrimidin-1-yl)-5-methoxy-3-quinolyl]phenyl]methanesulfonamide

Guidance literature:: Multi-step reaction with 10 steps

1.1: diisobutylaluminium hydride / dichloromethane / 0 °C / Inert atmosphere

2.1: carbon tetrabromide; triphenylphosphine / dichloromethane / 19 h / 20 °C / Inert atmosphere

3.1: dichloromethane; water / 0.25 h / Inert atmosphere; Reflux

4.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / 20 °C / Inert atmosphere

5.1: diisobutylaluminium hydride / dichloromethane / 1 h / -78 °C / Inert atmosphere

5.2: Inert atmosphere

6.1: diethylamino-sulfur trifluoride / dichloromethane / 72 h / 20 °C / Inert atmosphere

7.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / methanol; toluene / 1 h / 120 °C / Inert atmosphere; Microwave irradiation

8.1: tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; tert-butyl XPhos; sodium t-butanolate / toluene / 72 h / 20 °C / Inert atmosphere

9.1: hydrogenchloride / dichloromethane; 1,4-dioxane / 1 h / 20 °C / Inert atmosphere

10.1: toluene / 0.5 h / 130 °C / Inert atmosphere

10.2: 0.75 h / 0 °C / Inert atmosphere

10.3: 1.5 h / 110 °C / Inert atmosphere

With hydrogenchloride; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; tetrakis(triphenylphosphine) palladium⁽⁰⁾; carbon tetrabromide; diethylamino-sulfur trifluoride; sodium hydride; diisobutylaluminium hydride; sodium carbonate; triphenylphosphine; sodium t-butanolate; tert-butyl XPhos; In 1,4-dioxane; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; mineral oil;
DOI:10.1021/jm401329s