(1R,4R,6R)-3-{[5-methyl-2-(2-pyrimidinyl)phenyl]carbonyl}-4-{2-[5-(trifluoromethyl)-2-pyridinyl]ethyl}-3-azabicyclo[4.1.0]heptane

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Chemical Name:(1R,4R,6R)-3-{[5-methyl-2-(2-pyrimidinyl)phenyl]carbonyl}-4-{2-[5-(trifluoromethyl)-2-pyridinyl]ethyl}-3-azabicyclo[4.1.0]heptane
CAS No.:1384261-53-3
Molecular Formula:C₂₆H₂₅F₃N₄O
Molecular Weight:466.506
Hs Code.:

Synonyms:(1R,4R,6R)-3-{[5-methyl-2-(2-pyrimidinyl)phenyl]carbonyl}-4-{2-[5-(trifluoromethyl)-2-pyridinyl]ethyl}-3-azabicyclo[4.1.0]heptane

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Chemical Property of (1R,4R,6R)-3-{[5-methyl-2-(2-pyrimidinyl)phenyl]carbonyl}-4-{2-[5-(trifluoromethyl)-2-pyridinyl]ethyl}-3-azabicyclo[4.1.0]heptane

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Technology Process of (1R,4R,6R)-3-{[5-methyl-2-(2-pyrimidinyl)phenyl]carbonyl}-4-{2-[5-(trifluoromethyl)-2-pyridinyl]ethyl}-3-azabicyclo[4.1.0]heptane

There total 13 articles about (1R,4R,6R)-3-{[5-methyl-2-(2-pyrimidinyl)phenyl]carbonyl}-4-{2-[5-(trifluoromethyl)-2-pyridinyl]ethyl}-3-azabicyclo[4.1.0]heptane 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:

: 1088994-22-2
5-methyl-2-(pyrimidin-2-yl)benzoic acid

: 1384261-80-6
(1R,4R,6R)-4-{2-[5-(trifluoromethyl)-2-pyridinyl]ethyl}-3-azabicyclo[4.1.0]heptane

: 1384261-53-3
(1R,4R,6R)-3-{[5-methyl-2-(2-pyrimidinyl)phenyl]carbonyl}-4-{2-[5-(trifluoromethyl)-2-pyridinyl]ethyl}-3-azabicyclo[4.1.0]heptane

Guidance literature:: 5-methyl-2-(pyrimidin-2-yl)benzoic acid; (1R,4R,6R)-4-{2-[5-(trifluoromethyl)-2-pyridinyl]ethyl}-3-azabicyclo[4.1.0]heptane; With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine; In dichloromethane; for 10h; Reflux;

With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; In N,N-dimethyl-formamide; at 90 ℃; for 1h;

Reference yield:

: 89395-28-8
(1R,5S)-3-oxabicyclo[3.1.0]hexan-2-one

: 1384261-53-3
(1R,4R,6R)-3-{[5-methyl-2-(2-pyrimidinyl)phenyl]carbonyl}-4-{2-[5-(trifluoromethyl)-2-pyridinyl]ethyl}-3-azabicyclo[4.1.0]heptane

Guidance literature:: Multi-step reaction with 13 steps

1.1: chloro-trimethyl-silane; sodium iodide / acetonitrile / 3.83 h / 20 - 50 °C / Inert atmosphere

1.2: 15.5 h / 20 °C / Inert atmosphere

2.1: potassium tert-butylate / 2-methyltetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere

2.2: 2.92 h / 0 - 5 °C / Inert atmosphere

2.3: 16.33 h / 0 - 20 °C

3.1: hydrogenchloride / toluene; water / 20 h / 105 °C

4.1: potassium hydroxide / toluene; methanol / 3 h / 15 - 20 °C

4.2: 10 - 20 °C

4.3: pH 5.5

5.1: lithium borohydride; boron trifluoride-tetrahydrofuran complex / tetrahydrofuran / 17 h / 25 - 30 °C

5.2: 1 h / 25 - 50 °C

6.1: sodium hydroxide / water; tetrahydrofuran / 3.5 h / 25 °C / pH 8.5 - 9

7.1: Dess-Martin periodane / dichloromethane / 3 h / 20 °C / Inert atmosphere

8.1: triphenylphosphine / dichloromethane / 0.5 h / 0 °C

9.1: sec.-butyllithium / tetrahydrofuran / 3 h / -78 °C / Inert atmosphere

10.1: N-ethyl-N,N-diisopropylamine; copper(l) iodide / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / N,N-dimethyl-formamide / 3 h / 23 °C

11.1: hydrogen / palladium on activated charcoal / methanol / 5 h

12.1: trifluoroacetic acid / dichloromethane / 1 h

13.1: N-ethyl-N,N-diisopropylamine; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide / dichloromethane / 10 h / Reflux

13.2: 1 h / 90 °C

With copper(l) iodide; lithium borohydride; chloro-trimethyl-silane; boron trifluoride-tetrahydrofuran complex; potassium tert-butylate; hydrogen; sec.-butyllithium; Dess-Martin periodane; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine; triphenylphosphine; trifluoroacetic acid; sodium iodide; potassium hydroxide; sodium hydroxide; hydrogenchloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; palladium on activated charcoal; In tetrahydrofuran; 2-methyltetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile;

Reference yield:

: C₇H₁₃NO

: 1384261-53-3
(1R,4R,6R)-3-{[5-methyl-2-(2-pyrimidinyl)phenyl]carbonyl}-4-{2-[5-(trifluoromethyl)-2-pyridinyl]ethyl}-3-azabicyclo[4.1.0]heptane

Guidance literature:: Multi-step reaction with 8 steps

1.1: sodium hydroxide / water; tetrahydrofuran / 3.5 h / 25 °C / pH 8.5 - 9

2.1: Dess-Martin periodane / dichloromethane / 3 h / 20 °C / Inert atmosphere

3.1: triphenylphosphine / dichloromethane / 0.5 h / 0 °C

4.1: sec.-butyllithium / tetrahydrofuran / 3 h / -78 °C / Inert atmosphere

5.1: N-ethyl-N,N-diisopropylamine; copper(l) iodide / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / N,N-dimethyl-formamide / 3 h / 23 °C

6.1: hydrogen / palladium on activated charcoal / methanol / 5 h

7.1: trifluoroacetic acid / dichloromethane / 1 h

8.1: N-ethyl-N,N-diisopropylamine; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide / dichloromethane / 10 h / Reflux

8.2: 1 h / 90 °C

With copper(l) iodide; hydrogen; sec.-butyllithium; Dess-Martin periodane; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine; triphenylphosphine; trifluoroacetic acid; sodium hydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;