(S)-1-(3-fluoro-4-(trifluoromethyl)phenyl)-N-((S)-1,1,1-trifluoropropan-2-yl)-3,4-dihydroisoquinoline-2(1H)-carboxamide

Base Information

• Chemical Name: (S)-1-(3-fluoro-4-(trifluoromethyl)phenyl)-N-((S)-1,1,1-trifluoropropan-2-yl)-3,4-dihydroisoquinoline-2(1H)-carboxamide
• CAS No.: 1589602-11-8
• Molecular Formula: C₁₉H₁₆F₇N₃O
• Molecular Weight: 435.344

Synonyms:(S)-1-(3-fluoro-4-(trifluoromethyl)phenyl)-N-((S)-1,1,1-trifluoropropan-2-yl)-3,4-dihydroisoquinoline-2(1H)-carboxamide

Chemical Property of (S)-1-(3-fluoro-4-(trifluoromethyl)phenyl)-N-((S)-1,1,1-trifluoropropan-2-yl)-3,4-dihydroisoquinoline-2(1H)-carboxamide

Chemical Property:

Purity/Quality:

Safty Information:

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Useful:

Technology Process of (S)-1-(3-fluoro-4-(trifluoromethyl)phenyl)-N-((S)-1,1,1-trifluoropropan-2-yl)-3,4-dihydroisoquinoline-2(1H)-carboxamide

There total 7 articles about (S)-1-(3-fluoro-4-(trifluoromethyl)phenyl)-N-((S)-1,1,1-trifluoropropan-2-yl)-3,4-dihydroisoquinoline-2(1H)-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: 36.3%

(S)-1,1,1-trifluoropropan-2-amine (125278-10-6,779303-24-1) + 8-(3-fluoro-4-(trifluoromethyl)phenyl)-5,6,7,8-tetrahydro-1,7-naphthyridine (1589601-99-9) + 1,1'-carbonyldiimidazole (530-62-1) → (S)-1-(3-fluoro-4-(trifluoromethyl)phenyl)-N-((S)-1,1,1-trifluoropropan-2-yl)-3,4-dihydroisoquinoline-2(1H)-carboxamide (1589602-11-8) + (R)-1-(3-fluoro-4-(trifluoromethyl)phenyl)-N-((S)-1,1,1-trifluoropropan-2-yl)-3,4-dihydroisoquinoline-2(1H)-carboxamide (1589602-10-7)

Guidance literature:

(S)-1,1,1-trifluoropropan-2-amine; 1,1'-carbonyldiimidazole; In dichloromethane; at 20 ℃; for 1.15h; Inert atmosphere;

8-(3-fluoro-4-(trifluoromethyl)phenyl)-5,6,7,8-tetrahydro-1,7-naphthyridine; With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃; for 22h; Inert atmosphere;

DOI:10.1021/jm401955h

Reference yield:

3-bromopicolinaldehyde (405174-97-2) → (S)-1-(3-fluoro-4-(trifluoromethyl)phenyl)-N-((S)-1,1,1-trifluoropropan-2-yl)-3,4-dihydroisoquinoline-2(1H)-carboxamide (1589602-11-8) + (R)-1-(3-fluoro-4-(trifluoromethyl)phenyl)-N-((S)-1,1,1-trifluoropropan-2-yl)-3,4-dihydroisoquinoline-2(1H)-carboxamide (1589602-10-7)

Guidance literature:

Multi-step reaction with 5 steps

1.1: bis(triphenylphosphine)palladium(II) chloride; copper(l) iodide; triethylamine / N,N-dimethyl-formamide / 1.5 h / 20 °C

2.1: ammonia / ethanol / 2 h / 80 °C / Sealed tube

3.1: diisobutylaluminium hydride / diethyl ether; hexane / 1 h / 20 °C / Cooling with ice

3.2: 2 h / 20 °C / Cooling with ice

4.1: hydrogenchloride; palladium 10% on activated carbon; hydrogen / ethanol; isopropyl alcohol / 16 h / 20 °C / 760.05 Torr

5.1: dichloromethane / 1.15 h / 20 °C / Inert atmosphere

5.2: 22 h / 20 °C / Inert atmosphere

With hydrogenchloride; copper(l) iodide; bis(triphenylphosphine)palladium(II) chloride; palladium 10% on activated carbon; ammonia; hydrogen; diisobutylaluminium hydride; triethylamine; In diethyl ether; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; isopropyl alcohol;

DOI:10.1021/jm401955h

Reference yield:

3-bromo-2-picoline (38749-79-0) → (S)-1-(3-fluoro-4-(trifluoromethyl)phenyl)-N-((S)-1,1,1-trifluoropropan-2-yl)-3,4-dihydroisoquinoline-2(1H)-carboxamide (1589602-11-8) + (R)-1-(3-fluoro-4-(trifluoromethyl)phenyl)-N-((S)-1,1,1-trifluoropropan-2-yl)-3,4-dihydroisoquinoline-2(1H)-carboxamide (1589602-10-7)

Guidance literature:

Multi-step reaction with 7 steps

1.1: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / 30 h / Reflux

2.1: morpholine / 1 h / 60 °C

3.1: bis(triphenylphosphine)palladium(II) chloride; copper(l) iodide; triethylamine / N,N-dimethyl-formamide / 1.5 h / 20 °C

4.1: ammonia / ethanol / 2 h / 80 °C / Sealed tube

5.1: diisobutylaluminium hydride / diethyl ether; hexane / 1 h / 20 °C / Cooling with ice

5.2: 2 h / 20 °C / Cooling with ice

6.1: hydrogenchloride; palladium 10% on activated carbon; hydrogen / ethanol; isopropyl alcohol / 16 h / 20 °C / 760.05 Torr

7.1: dichloromethane / 1.15 h / 20 °C / Inert atmosphere

7.2: 22 h / 20 °C / Inert atmosphere

With morpholine; hydrogenchloride; N-Bromosuccinimide; copper(l) iodide; bis(triphenylphosphine)palladium(II) chloride; palladium 10% on activated carbon; ammonia; hydrogen; diisobutylaluminium hydride; triethylamine; dibenzoyl peroxide; In tetrachloromethane; diethyl ether; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; isopropyl alcohol;

DOI:10.1021/jm401955h

upstream raw materials:

3-bromopicolinaldehyde

3-((trimethylsilyl)ethynyl)-2-pyridinecarboxaldehyde

[1,7]naphthyridine

(S)-1,1,1-trifluoropropan-2-amine

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