(1S,2S)-N₁-(2-(5-chloro-1-tosyl-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-1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoropyrimidin-4-yl)cyclohexane-1,2-diamine
• CAS No.: 1259277-58-1
• Molecular Formula: C₂₄H₂₄ClFN₆O₂S
• Molecular Weight: 515.011

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

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

There total 6 articles about (1S,2S)-N₁-(2-(5-chloro-1-tosyl-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: 79.0%

5-chloro-3-(5-fluoro-4-methylsulfinyl-pyrimidin-2-yl)-1-(p-tolylsulfonyl)pyrrolo[2,3-b]pyridine (1259012-01-5) + (S,S)-1,2-diaminocyclohexane (21436-03-3) → (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)

Guidance literature:

In tetrahydrofuran; at 140 ℃; for 0.333333h; Sealed tube;

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-1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoropyrimidin-4-yl)cyclohexane-1,2-diamine (1259277-58-1)

Guidance literature:

Multi-step reaction with 2 steps

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

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

With 3-chloro-benzenecarboperoxoic acid; 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-1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoropyrimidin-4-yl)cyclohexane-1,2-diamine (1259277-58-1)

Guidance literature:

Multi-step reaction with 3 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

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

DOI:10.1021/jm5007275

upstream raw materials:

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

(S,S)-1,2-diaminocyclohexane

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

Downstream raw materials:

N-[(1S, 2S)-2-[[2-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoropyrimidin-4-yl]amino]cyclohexyl]acetamide

methyl (1S,2S)-2-(2-(5-chloro-1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoro-pyrimidin-4-ylamino)cyclohexylcarbamate

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

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