3-[(2S,4R)-1-acetyl-2-methyl-4-(3-pyridinylamino)-1,2,3,4-tetrahydro-6-quinolinyl]-N,N-dimethylbenzamide

Base Information

Chemical Name:3-[(2S,4R)-1-acetyl-2-methyl-4-(3-pyridinylamino)-1,2,3,4-tetrahydro-6-quinolinyl]-N,N-dimethylbenzamide
CAS No.:1300694-41-0
Molecular Formula:C₂₆H₂₈N₄O₂
Molecular Weight:428.534
Hs Code.:

Synonyms:3-[(2S,4R)-1-acetyl-2-methyl-4-(3-pyridinylamino)-1,2,3,4-tetrahydro-6-quinolinyl]-N,N-dimethylbenzamide

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Chemical Property of 3-[(2S,4R)-1-acetyl-2-methyl-4-(3-pyridinylamino)-1,2,3,4-tetrahydro-6-quinolinyl]-N,N-dimethylbenzamide

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Technology Process of 3-[(2S,4R)-1-acetyl-2-methyl-4-(3-pyridinylamino)-1,2,3,4-tetrahydro-6-quinolinyl]-N,N-dimethylbenzamide

There total 12 articles about 3-[(2S,4R)-1-acetyl-2-methyl-4-(3-pyridinylamino)-1,2,3,4-tetrahydro-6-quinolinyl]-N,N-dimethylbenzamide 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: 59.3%

: 1300694-38-5
C₂₄H₂₃N₃O₃

: 124-40-3
dimethyl amine

: 1300694-41-0
3-[(2S,4R)-1-acetyl-2-methyl-4-(3-pyridinylamino)-1,2,3,4-tetrahydro-6-quinolinyl]-N,N-dimethylbenzamide

Guidance literature:: With N-ethyl-N,N-diisopropylamine; HATU; In tetrahydrofuran; N,N-dimethyl-formamide; at 20 ℃; for 0.916667h;

Reference yield:

: 106-40-1
4-bromo-aniline

: 1300694-41-0
3-[(2S,4R)-1-acetyl-2-methyl-4-(3-pyridinylamino)-1,2,3,4-tetrahydro-6-quinolinyl]-N,N-dimethylbenzamide

Guidance literature:: Multi-step reaction with 8 steps

1.1: (R-BINAP)ditriflatebis(acetonitrile)palladium(ll) / toluene / 0.33 h / Inert atmosphere

1.2: 16 h

2.1: sodium tetrahydroborate; magnesium(II) chloride hexahydrate; water / ethanol / 2 h / -10 - 20 °C

2.2: 1 h / 20 °C

3.1: pyridine / dichloromethane / 16 h / 20 °C / Inert atmosphere

4.1: sodium hydrogencarbonate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / 1,4-dioxane; water / 1 h / 100 °C / Inert atmosphere; Microwave irradiation

5.1: aluminum (III) chloride / dichloromethane / 0.5 h / 0 °C / Cooling with ice

5.2: 0.33 h / 0 °C

6.1: triethylamine / copper diacetate / dichloromethane / 0.17 h / 20 °C

6.2: 734 h / 20 °C

7.1: water; sodium hydroxide / methanol / 4 h / 20 °C

8.1: N-ethyl-N,N-diisopropylamine; HATU / tetrahydrofuran; N,N-dimethyl-formamide / 0.92 h / 20 °C

With pyridine; aluminum (III) chloride; sodium tetrahydroborate; magnesium(II) chloride hexahydrate; water; sodium hydrogencarbonate; triethylamine; N-ethyl-N,N-diisopropylamine; HATU; sodium hydroxide; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; (R-BINAP)ditriflatebis(acetonitrile)palladium(ll); copper diacetate; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene;

Reference yield:

: 108-86-1,52753-63-6
bromobenzene

: 1300694-41-0
3-[(2S,4R)-1-acetyl-2-methyl-4-(3-pyridinylamino)-1,2,3,4-tetrahydro-6-quinolinyl]-N,N-dimethylbenzamide

Guidance literature:: Multi-step reaction with 11 steps

1.1: caesium carbonate / toluene / 0.75 h / Inert atmosphere

1.2: 16.75 h / 80 °C / Inert atmosphere

2.1: N-Bromosuccinimide / N,N-dimethyl-formamide / 0.33 h / Inert atmosphere; Cooling with ice

3.1: sulfuric acid / toluene / 2 h / 60 °C

4.1: lithium tert-butoxide / tetrahydrofuran; ethyl acetate / 0.5 h

5.1: sodium tetrahydroborate; magnesium(II) chloride hexahydrate; water / ethanol / 2 h / -10 - 20 °C

5.2: 1 h / 20 °C

6.1: pyridine / dichloromethane / 16 h / 20 °C / Inert atmosphere

7.1: sodium hydrogencarbonate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / 1,4-dioxane; water / 1 h / 100 °C / Inert atmosphere; Microwave irradiation

8.1: aluminum (III) chloride / dichloromethane / 0.5 h / 0 °C / Cooling with ice

8.2: 0.33 h / 0 °C

9.1: triethylamine / copper diacetate / dichloromethane / 0.17 h / 20 °C

9.2: 734 h / 20 °C

10.1: water; sodium hydroxide / methanol / 4 h / 20 °C

11.1: N-ethyl-N,N-diisopropylamine; HATU / tetrahydrofuran; N,N-dimethyl-formamide / 0.92 h / 20 °C

With pyridine; aluminum (III) chloride; sodium tetrahydroborate; N-Bromosuccinimide; magnesium(II) chloride hexahydrate; sulfuric acid; water; sodium hydrogencarbonate; caesium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; HATU; sodium hydroxide; lithium tert-butoxide; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; copper diacetate; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; toluene;