1,3-dimethyl-4-[3-(pyrrolidin-3-yloxy)-phenylamino]-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid amide

Base Information

• Chemical Name: 1,3-dimethyl-4-[3-(pyrrolidin-3-yloxy)-phenylamino]-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid amide
• CAS No.: 389058-61-1
• Molecular Formula: C₁₉H₂₂N₆O₂
• Molecular Weight: 366.423
• Mol file: 389058-61-1.mol

Synonyms:1,3-dimethyl-4-[3-(pyrrolidin-3-yloxy)-phenylamino]-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid amide

Chemical Property of 1,3-dimethyl-4-[3-(pyrrolidin-3-yloxy)-phenylamino]-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid amide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1,3-dimethyl-4-[3-(pyrrolidin-3-yloxy)-phenylamino]-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid amide

There total 10 articles about 1,3-dimethyl-4-[3-(pyrrolidin-3-yloxy)-phenylamino]-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid amide 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: 53.0%

3-[3-(5-carbamoyl-1,3-dimethyl-1H-pyrazolo[3,4-b]pyridin-4-ylamino)-phenoxy]-pyrrolidine-1-carboxylic acid tert-butyl ester (389058-54-2) → 1,3-dimethyl-4-[3-(pyrrolidin-3-yloxy)-phenylamino]-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid amide (389058-61-1)

Guidance literature:

With hydrogenchloride; In methanol; ethyl acetate; at 20 ℃; for 15h;

DOI:10.1016/j.bmc.2004.05.032

Reference yield:

meta-nitrophenol (554-84-7) → 1,3-dimethyl-4-[3-(pyrrolidin-3-yloxy)-phenylamino]-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid amide (389058-61-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 75 percent / PPh₃; DEAD / tetrahydrofuran / 20 °C

2: 85 percent / H₂ / Pd/C / methanol / 3 h / atmosperic pressure

3: 100 percent / dioxane / 1 h / 120 °C

4: 53 percent / HCl / methanol; ethyl acetate / 15 h / 20 °C

With hydrogenchloride; hydrogen; triphenylphosphine; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; ethyl acetate;

DOI:10.1016/j.bmc.2004.05.032

Reference yield:

5-Amino-1,3-dimethylpyrazole (3524-32-1) → 1,3-dimethyl-4-[3-(pyrrolidin-3-yloxy)-phenylamino]-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid amide (389058-61-1)

Guidance literature:

Multi-step reaction with 7 steps

1: 89 percent / 1 h / 120 °C

2: 77 percent / POCl₃ / 18 h / 120 °C

3: 99 percent / potassium hydroxide / H₂O; 1,2-dimethoxy-ethane / 18 h / 20 °C

4: SOCl₂ / 1 h / 80 °C

5: 1.98 g / aq. ammonium / tetrahydrofuran / 0.17 h / 0 °C

6: 100 percent / dioxane / 1 h / 120 °C

7: 53 percent / HCl / methanol; ethyl acetate / 15 h / 20 °C

With hydrogenchloride; potassium hydroxide; ammonium hydroxide; thionyl chloride; trichlorophosphate; In tetrahydrofuran; 1,4-dioxane; methanol; 1,2-dimethoxyethane; water; ethyl acetate;

DOI:10.1016/j.bmc.2004.05.032

upstream raw materials:

4-chloro-1,3-dimethyl-1H-pyrazolo[3,4-b]pyridine-5-carboxamide

3-[3-(5-carbamoyl-1,3-dimethyl-1H-pyrazolo[3,4-b]pyridin-4-ylamino)-phenoxy]-pyrrolidine-1-carboxylic acid tert-butyl ester

5-Amino-1,3-dimethylpyrazole

meta-nitrophenol