(1S,2S)-N₁-(2-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoropyrimidin-4-yl)cyclohexane-1,2-diamine

Base Information

• Chemical Name: (1S,2S)-N₁-(2-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoropyrimidin-4-yl)cyclohexane-1,2-diamine
• CAS No.: 1259278-56-2
• Molecular Formula: C₁₇H₁₈ClFN₆
• Molecular Weight: 360.822

Synonyms:(1S,2S)-N₁-(2-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoropyrimidin-4-yl)cyclohexane-1,2-diamine

Chemical Property of (1S,2S)-N₁-(2-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoropyrimidin-4-yl)cyclohexane-1,2-diamine

Chemical Property:

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Technology Process of (1S,2S)-N₁-(2-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoropyrimidin-4-yl)cyclohexane-1,2-diamine

There total 5 articles about (1S,2S)-N₁-(2-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoropyrimidin-4-yl)cyclohexane-1,2-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: 72.0%

(1S,2S)-N1-(2-(5-chloro-1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoropyrimidin-4-yl)cyclohexane-1,2-diamine (1259277-58-1) → (1S,2S)-N1-(2-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoropyrimidin-4-yl)cyclohexane-1,2-diamine (1259278-56-2)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; at 150 ℃; for 0.166667h; Microwave irradiation;

DOI:10.1021/jm5007275

Reference yield:

5-chloro-3-(5-fluoro-4-(methylthio)pyrimidin-2-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine → (1S,2S)-N1-(2-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoropyrimidin-4-yl)cyclohexane-1,2-diamine (1259278-56-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 4 h / 0 - 20 °C

2: tetrahydrofuran / 0.33 h / 140 °C / Sealed tube

3: lithium hydroxide / tetrahydrofuran / 0.17 h / 150 °C / Microwave irradiation

With 3-chloro-benzenecarboperoxoic acid; lithium hydroxide; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jm5007275

Reference yield:

5-chloro-1-(p-tolylsulfonyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrrolo[2,3-b]pyridine (866546-11-4) → (1S,2S)-N1-(2-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoropyrimidin-4-yl)cyclohexane-1,2-diamine (1259278-56-2)

Guidance literature:

Multi-step reaction with 4 steps

1: sodium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / water; 1,2-dimethoxyethane / 0.25 h / 125 °C / Inert atmosphere; Sealed tube

2: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 4 h / 0 - 20 °C

3: tetrahydrofuran / 0.33 h / 140 °C / Sealed tube

4: lithium hydroxide / tetrahydrofuran / 0.17 h / 150 °C / Microwave irradiation

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate; 3-chloro-benzenecarboperoxoic acid; lithium hydroxide; In tetrahydrofuran; 1,2-dimethoxyethane; dichloromethane; water;

DOI:10.1021/jm5007275

upstream raw materials:

5-chloro-1-(p-tolylsulfonyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrrolo[2,3-b]pyridine

3-bromo-5-chloro-1 H-pyrrolo[2,3-b]pyridine

3-bromo-5-chloro-1-tosyl-1H-pyrrolo[2,3-b]pyridine

(1S,2S)-N₁-(2-(5-chloro-1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoropyrimidin-4-yl)cyclohexane-1,2-diamine

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