tert-butyl 1-(5-(1-(4-chlorophenyl)-4-(hydroxymethyl)-1H-pyrazole-3-carboxamido)pyridin-2-yl)pyrrolidin-3-yl(methyl)carbamate

Base Information

• Chemical Name: tert-butyl 1-(5-(1-(4-chlorophenyl)-4-(hydroxymethyl)-1H-pyrazole-3-carboxamido)pyridin-2-yl)pyrrolidin-3-yl(methyl)carbamate
• CAS No.: 1224172-22-8
• Molecular Formula: C₂₆H₃₁ClN₆O₄
• Molecular Weight: 527.023
• Mol file: 1224172-22-8.mol

Synonyms:tert-butyl 1-(5-(1-(4-chlorophenyl)-4-(hydroxymethyl)-1H-pyrazole-3-carboxamido)pyridin-2-yl)pyrrolidin-3-yl(methyl)carbamate

Chemical Property of tert-butyl 1-(5-(1-(4-chlorophenyl)-4-(hydroxymethyl)-1H-pyrazole-3-carboxamido)pyridin-2-yl)pyrrolidin-3-yl(methyl)carbamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl 1-(5-(1-(4-chlorophenyl)-4-(hydroxymethyl)-1H-pyrazole-3-carboxamido)pyridin-2-yl)pyrrolidin-3-yl(methyl)carbamate

There total 6 articles about tert-butyl 1-(5-(1-(4-chlorophenyl)-4-(hydroxymethyl)-1H-pyrazole-3-carboxamido)pyridin-2-yl)pyrrolidin-3-yl(methyl)carbamate 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: 64.0%

ethyl 3-(6-(3-(tert-butoxycarbonyl(methyl)amino)pyrrolidin-1-yl)pyridin-3-ylcarbamoyl)-1-(4-chlorophenyl)-1H-pyrazole-4-carboxylate (1224172-21-7) → tert-butyl 1-(5-(1-(4-chlorophenyl)-4-(hydroxymethyl)-1H-pyrazole-3-carboxamido)pyridin-2-yl)pyrrolidin-3-yl(methyl)carbamate (1224172-22-8)

Guidance literature:

ethyl 3-(6-(3-(tert-butoxycarbonyl(methyl)amino)pyrrolidin-1-yl)pyridin-3-ylcarbamoyl)-1-(4-chlorophenyl)-1H-pyrazole-4-carboxylate; With lithium borohydride; In tetrahydrofuran; at 20 ℃; for 3h;

With sodium hydrogencarbonate; In tetrahydrofuran;

Reference yield:

ethyl 1-(4-chlorophenyl)-4-formyl-1H-pyrazole-3-carboxylate (1156510-03-0) → tert-butyl 1-(5-(1-(4-chlorophenyl)-4-(hydroxymethyl)-1H-pyrazole-3-carboxamido)pyridin-2-yl)pyrrolidin-3-yl(methyl)carbamate (1224172-22-8)

Guidance literature:

Multi-step reaction with 3 steps

1: sodium tetrahydroborate / tetrahydrofuran / 2 h / 0 °C

2: sodium hydroxide / water / 2 h / Reflux

3: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / 16 h / 20 °C

With sodium tetrahydroborate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; sodium hydroxide; In tetrahydrofuran; water;

DOI:10.1016/j.bmcl.2015.05.008

Reference yield:

ethyl 1-(4-chlorophenyl)-4-(hydroxymethyl)-1H-pyrazole-3-carboxylate (1224172-25-1) → tert-butyl 1-(5-(1-(4-chlorophenyl)-4-(hydroxymethyl)-1H-pyrazole-3-carboxamido)pyridin-2-yl)pyrrolidin-3-yl(methyl)carbamate (1224172-22-8)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium hydroxide / water / 2 h / Reflux

2: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / 16 h / 20 °C

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; sodium hydroxide; In water;

DOI:10.1016/j.bmcl.2015.05.008

upstream raw materials:

ethyl 3-(6-(3-(tert-butoxycarbonyl(methyl)amino)pyrrolidin-1-yl)pyridin-3-ylcarbamoyl)-1-(4-chlorophenyl)-1H-pyrazole-4-carboxylate

ethyl 1-(4-chlorophenyl)-4-formyl-1H-pyrazole-3-carboxylate

ethyl 1-(4-chlorophenyl)-4-(hydroxymethyl)-1H-pyrazole-3-carboxylate

tert-butyl [1-(5-aminopyridin-2-yl)pyrrolidin-3-yl](methyl)carbamate

Downstream raw materials:

tert-butyl 1-(5-(4-(chloromethyl)-1-(4-chlorophenyl)-1H-pyrazole-3-carboxamido)pyridin-2-yl)pyrrolidin-3-yl(methyl)carbamate

tert-butyl 1-(5-(2-(4-chlorophenyl)-6-oxopyrrolo[3,4-c]pyrazol-5(2H,4H,6H)-yl)pyridin-2-yl)pyrrolidin-3-yl(methyl)carbamate

2-(4-chlorophenyl)-5-(6-(3-(methylamino)pyrrolidin-1-yl)pyridin-3-yl)-4,5-dihydropyrrolo[3,4-c]pyrazol-6(2H)-one