1-benzyl-1H-pyrazol-4-carboxylic acid [4-((3R,4R)-3-amino-4-cyclopropylpiperidin-1-yl)-5-bromo-1H-pyrrolo[2,3-b]pyridin-3-yl]amide

Base Information

• Chemical Name: 1-benzyl-1H-pyrazol-4-carboxylic acid [4-((3R,4R)-3-amino-4-cyclopropylpiperidin-1-yl)-5-bromo-1H-pyrrolo[2,3-b]pyridin-3-yl]amide
• CAS No.: 1449320-47-1
• Molecular Formula: C₂₆H₂₈BrN₇O
• Molecular Weight: 534.459
• Mol file: 1449320-47-1.mol

Synonyms:1-benzyl-1H-pyrazol-4-carboxylic acid [4-((3R,4R)-3-amino-4-cyclopropylpiperidin-1-yl)-5-bromo-1H-pyrrolo[2,3-b]pyridin-3-yl]amide

Chemical Property of 1-benzyl-1H-pyrazol-4-carboxylic acid [4-((3R,4R)-3-amino-4-cyclopropylpiperidin-1-yl)-5-bromo-1H-pyrrolo[2,3-b]pyridin-3-yl]amide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-benzyl-1H-pyrazol-4-carboxylic acid [4-((3R,4R)-3-amino-4-cyclopropylpiperidin-1-yl)-5-bromo-1H-pyrrolo[2,3-b]pyridin-3-yl]amide

There total 10 articles about 1-benzyl-1H-pyrazol-4-carboxylic acid [4-((3R,4R)-3-amino-4-cyclopropylpiperidin-1-yl)-5-bromo-1H-pyrrolo[2,3-b]pyridin-3-yl]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: 2.84%

1-benzyl-1H-pyrazol-4-carboxylic acid (5-bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)amide (1449318-35-7) + ((3R,4R)-4-cyclopropylpiperidin-3-yl)phosphoramidic acid diethyl ester (1449320-49-3) → 1-benzyl-1H-pyrazol-4-carboxylic acid [4-((3R,4R)-3-amino-4-cyclopropylpiperidin-1-yl)-5-bromo-1H-pyrrolo[2,3-b]pyridin-3-yl]amide (1449320-47-1)

Guidance literature:

1-benzyl-1H-pyrazol-4-carboxylic acid (5-bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)amide; ((3R,4R)-4-cyclopropylpiperidin-3-yl)phosphoramidic acid diethyl ester; In butan-1-ol; at 160 ℃; for 60h; Sealed tube;

With methanol; In dichloromethane; butan-1-ol;

Reference yield: 2.84%

((3R,4R)-4-cyclopropylpiperidin-3-yl)phosphoramidic acid diethyl ester (1449320-49-3) + 1-benzyl-1H-pyrazol-4-carboxylic acid (5-bromo-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)amide (1449318-54-0) → 1-benzyl-1H-pyrazol-4-carboxylic acid [4-((3R,4R)-3-amino-4-cyclopropylpiperidin-1-yl)-5-bromo-1H-pyrrolo[2,3-b]pyridin-3-yl]amide (1449320-47-1)

Guidance literature:

In butan-1-ol; at 160 ℃; for 60h;

Reference yield:

1,2,3,6-tetrahydropyridine (694-05-3) → 1-benzyl-1H-pyrazol-4-carboxylic acid [4-((3R,4R)-3-amino-4-cyclopropylpiperidin-1-yl)-5-bromo-1H-pyrrolo[2,3-b]pyridin-3-yl]amide (1449320-47-1)

Guidance literature:

Multi-step reaction with 6 steps

1.1: triethylamine / dichloromethane / 2.5 h / 0 - 20 °C

2.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 4.33 h / 5 - 20 °C

3.1: sodium azide; water; ammonium chloride / methanol / 18 h / 65 °C

3.2: 68 h / 0 - 20 °C

4.1: copper(l) iodide / tetrahydrofuran / 0.25 h / -30 °C

4.2: 2 h / -30 - 20 °C

5.1: hydrogen; palladium 10% on activated carbon / methanol / 5 h / Inert atmosphere

6.1: butan-1-ol / 60 h / 160 °C / Sealed tube

With copper(l) iodide; sodium azide; palladium 10% on activated carbon; water; hydrogen; ammonium chloride; triethylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; dichloromethane; butan-1-ol;

upstream raw materials:

1-benzyl-1H-pyrazol-4-carboxylic acid (5-bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)amide

((3R,4R)-4-cyclopropylpiperidin-3-yl)phosphoramidic acid diethyl ester

1,2,3,6-tetrahydropyridine

1-benzyloxycarbonyl-1,2,3,6-tetrahydropyridine

Refernces

• 1、 -. "1H-PYRROLO[2,3-B] PYRIDINE DERIVATIVES AND THEIR USE AS KINASE INHIBITORS". Page/Page column 93; 97; 98. . Retrieved 2013/08/15.