(1S,3R)-N₁-(5-fluoro-2-(5-fluoro-1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-4-yl)-N₃-(pyrazin-2-yl)cyclohexane-1,3-diamine

Base Information

• Chemical Name: (1S,3R)-N₁-(5-fluoro-2-(5-fluoro-1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-4-yl)-N₃-(pyrazin-2-yl)cyclohexane-1,3-diamine
• CAS No.: 1259367-36-6
• Molecular Formula: C₂₈H₂₆F₂N₈O₂S
• Molecular Weight: 576.63

Synonyms:(1S,3R)-N₁-(5-fluoro-2-(5-fluoro-1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-4-yl)-N₃-(pyrazin-2-yl)cyclohexane-1,3-diamine

Chemical Property of (1S,3R)-N₁-(5-fluoro-2-(5-fluoro-1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-4-yl)-N₃-(pyrazin-2-yl)cyclohexane-1,3-diamine

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Technology Process of (1S,3R)-N₁-(5-fluoro-2-(5-fluoro-1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-4-yl)-N₃-(pyrazin-2-yl)cyclohexane-1,3-diamine

There total 9 articles about (1S,3R)-N₁-(5-fluoro-2-(5-fluoro-1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-4-yl)-N₃-(pyrazin-2-yl)cyclohexane-1,3-diamine 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:

(1R,3S)-N1-(pyrazin-2-yl)cyclohexane-1,3-diamine (1259367-35-5) + 5-chloro-3-(5-fluoro-4-methylsulfinyl-pyrimidin-2-yl)-1-(p-tolylsulfonyl)pyrrolo[2,3-b]pyridine (1259012-01-5) → (1S,3R)-N1-(5-fluoro-2-(5-fluoro-1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-4-yl)-N3-(pyrazin-2-yl)cyclohexane-1,3-diamine (1259367-36-6)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol;

Reference yield:

(1R,3S)-N1-(pyrazin-2-yl)cyclohexane-1,3-diamine (1259367-35-5) + 5-fluoro-3-(5-fluoro-4-methylsulfinyl-pyrimidin-2-yl)-1-(p-tolylsulfonyl)-pyrrolo[2,3-b]pyridine (1259279-58-7) → (1S,3R)-N1-(5-fluoro-2-(5-fluoro-1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-4-yl)-N3-(pyrazin-2-yl)cyclohexane-1,3-diamine (1259367-36-6)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; Reflux;

Reference yield:

(1R,3S)-3-(((benzyloxy)carbonyl)amino)cyclohexanecarboxylic acid (952616-39-6) → (1S,3R)-N1-(5-fluoro-2-(5-fluoro-1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-4-yl)-N3-(pyrazin-2-yl)cyclohexane-1,3-diamine (1259367-36-6)

Guidance literature:

Multi-step reaction with 5 steps

1: pyridine; di-tert-butyl dicarbonate; ammonium bicarbonate

2: bis-[(trifluoroacetoxy)iodo]benzene / water; acetonitrile / 20 °C

3: caesium carbonate; copper(l) iodide / N,N-dimethyl-formamide / 20 °C / Inert atmosphere

4: palladium 10% on activated carbon; hydrogen / methanol / 3 h

5: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / Reflux

With pyridine; copper(l) iodide; di-tert-butyl dicarbonate; palladium 10% on activated carbon; hydrogen; ammonium bicarbonate; caesium carbonate; N-ethyl-N,N-diisopropylamine; bis-[(trifluoroacetoxy)iodo]benzene; In tetrahydrofuran; methanol; water; N,N-dimethyl-formamide; acetonitrile;

upstream raw materials:

(1R,3S)-N₁-(pyrazin-2-yl)cyclohexane-1,3-diamine

5-chloro-3-(5-fluoro-4-methylsulfinyl-pyrimidin-2-yl)-1-(p-tolylsulfonyl)pyrrolo[2,3-b]pyridine

(1S,3R)-3-ethoxycarbonylcyclohexane-1-carboxylic acid

ethyl (1R,3S)-3-benzyloxycarbonylaminocyclohexane-1-carboxylate

Downstream raw materials:

(1S,3R)-N₁-(5-fluoro-2-(5-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-4-yl)-N₃-(pyrazin-2-yl)cyclohexane-1,3-diamine

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