N-[5-[(5-chloro-4-pyrazolo[1,5-a]pyridin-3-ylpyrimidin-2-yl)amino]-2-[(3R)-3-dimethylaminopyrrolidin-1-yl]-4-methoxyphenyl]prop-2-enamide

Base Information

• Chemical Name: N-[5-[(5-chloro-4-pyrazolo[1,5-a]pyridin-3-ylpyrimidin-2-yl)amino]-2-[(3R)-3-dimethylaminopyrrolidin-1-yl]-4-methoxyphenyl]prop-2-enamide
• CAS No.: 1421373-41-2
• Molecular Formula: C₂₇H₂₉ClN₈O₂
• Molecular Weight: 533.033
• Mol file: 1421373-41-2.mol

Synonyms:N-[5-[(5-chloro-4-pyrazolo[1,5-a]pyridin-3-ylpyrimidin-2-yl)amino]-2-[(3R)-3-dimethylaminopyrrolidin-1-yl]-4-methoxyphenyl]prop-2-enamide

Chemical Property of N-[5-[(5-chloro-4-pyrazolo[1,5-a]pyridin-3-ylpyrimidin-2-yl)amino]-2-[(3R)-3-dimethylaminopyrrolidin-1-yl]-4-methoxyphenyl]prop-2-enamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-[5-[(5-chloro-4-pyrazolo[1,5-a]pyridin-3-ylpyrimidin-2-yl)amino]-2-[(3R)-3-dimethylaminopyrrolidin-1-yl]-4-methoxyphenyl]prop-2-enamide

There total 8 articles about N-[5-[(5-chloro-4-pyrazolo[1,5-a]pyridin-3-ylpyrimidin-2-yl)amino]-2-[(3R)-3-dimethylaminopyrrolidin-1-yl]-4-methoxyphenyl]prop-2-enamide 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: 58.0%

N-{5-chloro-(4-pyrazolo[1,5-a]pyridin-3-yl)-pyrimidin-2-yl}-4-[(3R)-3-dimethylaminopyrrolidin-1-yl]-6-methoxybenzene-1,3-diamine (1421372-06-6) + acryloyl chloride (814-68-6,25189-84-8) → N-[5-[(5-chloro-4-pyrazolo[1,5-a]pyridin-3-ylpyrimidin-2-yl)amino]-2-[(3R)-3-dimethylaminopyrrolidin-1-yl]-4-methoxyphenyl]prop-2-enamide (1421373-41-2)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; for 2h; Cooling with ice;

Reference yield:

5-chloro-N-(4-fluoro-2-methoxy-5-nitrophenyl)-4-(pyrazolo[1,5-a]pyridin-3-yl)pyrimidin-2-amine (1421372-08-8) → N-[5-[(5-chloro-4-pyrazolo[1,5-a]pyridin-3-ylpyrimidin-2-yl)amino]-2-[(3R)-3-dimethylaminopyrrolidin-1-yl]-4-methoxyphenyl]prop-2-enamide (1421373-41-2)

Guidance literature:

Multi-step reaction with 3 steps

1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 0.5 h / 140 °C / Microwave irradiation

2: iron; ammonium chloride / water; ethanol / 1.5 h / Reflux

3: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / Cooling with ice

With iron; ammonium chloride; N-ethyl-N,N-diisopropylamine; In ethanol; dichloromethane; N,N-dimethyl acetamide; water;

Reference yield:

5-chloro-N-[4-[(3R)-3-dimethylaminopyrrolidin-1-yl]-2-methoxy-5-nitrophenyl]-4-pyrazolo[1,5-a]pyridin-3-ylpyrimidin-2-amine (1421372-07-7) → N-[5-[(5-chloro-4-pyrazolo[1,5-a]pyridin-3-ylpyrimidin-2-yl)amino]-2-[(3R)-3-dimethylaminopyrrolidin-1-yl]-4-methoxyphenyl]prop-2-enamide (1421373-41-2)

Guidance literature:

Multi-step reaction with 2 steps

1: iron; ammonium chloride / water; ethanol / 1.5 h / Reflux

2: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / Cooling with ice

With iron; ammonium chloride; N-ethyl-N,N-diisopropylamine; In ethanol; dichloromethane; water;

upstream raw materials:

N-{5-chloro-(4-pyrazolo[1,5-a]pyridin-3-yl)-pyrimidin-2-yl}-4-[(3R)-3-dimethylaminopyrrolidin-1-yl]-6-methoxybenzene-1,3-diamine

acryloyl chloride

5-chloro-N-[4-[(3R)-3-dimethylaminopyrrolidin-1-yl]-2-methoxy-5-nitrophenyl]-4-pyrazolo[1,5-a]pyridin-3-ylpyrimidin-2-amine

5-chloro-N-(4-fluoro-2-methoxy-5-nitrophenyl)-4-(pyrazolo[1,5-a]pyridin-3-yl)pyrimidin-2-amine