6-[4-(tert-butoxycarbonyl)piperazin-1-yl]-5-chloronicotinic acid

Base Information

• Chemical Name: 6-[4-(tert-butoxycarbonyl)piperazin-1-yl]-5-chloronicotinic acid
• CAS No.: 683241-92-1
• Molecular Formula: C15H20ClN3O4
• Molecular Weight: 341.794
• Hs Code.: 2933599090
• Mol file: 683241-92-1.mol

Synonyms:6-[4-(tert-Butoxycarbonyl)piperazino]-5-chloronicotinic acid;6-[4-(tert-butoxycarbonyl)piperazin-1-yl]-5-chloronicotinic acid;4-(5-carboxy-3-chloro-pyridin-2-yl)-piperazine-1-carboxylic acid tert-butyl ester;

Chemical Property of 6-[4-(tert-butoxycarbonyl)piperazin-1-yl]-5-chloronicotinic acid

Chemical Property:

• Melting Point: 173～176℃
• Boiling Point: 505.2±50.0 °C(Predicted)
• PKA: 2.75±0.10(Predicted)
• PSA: 82.97000
• Density: 1.326±0.06 g/cm3(Predicted)
• LogP: 2.49320
• Storage Temp.: 2-8°C

Purity/Quality:

98%min ^*data from raw suppliers

6-[4-(tert-Butoxycarbonyl)piperazino]-5-chloronicotinic acid >95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 6-[4-(tert-butoxycarbonyl)piperazin-1-yl]-5-chloronicotinic acid

There total 5 articles about 6-[4-(tert-butoxycarbonyl)piperazin-1-yl]-5-chloronicotinic acid 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: 96.0%

5,6-dichloronicotinic acid (41667-95-2) + 1-t-Butoxycarbonylpiperazine (57260-71-6) → 6-(4-(tert-butoxycarbonyl)piperazin-1-yl)-5-chloronicotinic acid (683241-92-1)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl acetamide; at 120 ℃; for 20h;

Reference yield:

4-(3-chloro-5-methoxycarbonyl-pyridin-2-yl)piperazine-1-carboxylic acid tert-butyl ester (683241-93-2) → 6-(4-(tert-butoxycarbonyl)piperazin-1-yl)-5-chloronicotinic acid (683241-92-1)

Guidance literature:

With water; lithium hydroxide; In methanol; at 20 ℃; Combinatorial reaction / High throughput screening (HTS);

DOI:10.1016/j.bmcl.2009.07.020

Reference yield:

methyl 2,3-dichloro-pyridine-5-carboxylate (56055-54-0) → 6-(4-(tert-butoxycarbonyl)piperazin-1-yl)-5-chloronicotinic acid (683241-92-1)

Guidance literature:

Multi-step reaction with 2 steps

1: potassium carbonate / N,N-dimethyl-formamide / 90 °C

2: water; lithium hydroxide / methanol / 20 °C

With water; potassium carbonate; lithium hydroxide; In methanol; N,N-dimethyl-formamide;

DOI:10.1016/j.bmcl.2010.12.114

upstream raw materials:

5,6-dichloronicotinic acid

1-t-Butoxycarbonylpiperazine

4-(3-chloro-5-methoxycarbonyl-pyridin-2-yl)piperazine-1-carboxylic acid tert-butyl ester

methyl 2,3-dichloro-pyridine-5-carboxylate

Downstream raw materials:

tert-butyl 4-(3-chloro-5-((perfluorophenoxy)carbonyl)pyridin-2-yl)piperazine-1-carboxylate

Refernces

• 1、 Shao, Yuefei,Anilkumar, Gopinadhan N.,Carroll, Carolyn Diianni,Dong, Guizhen,Hall III, James W.,Hobbs, Doug W.,Jiang, Yueheng,Jenh, Chung-Her,Kim, Seong Heon,Kozlowski, Joseph A.,McGuinness, Brian F.,Rosenblum, Stuart B.,Schulman, Inna,Shih, Neng-Yang,Shu, Youheng,Wong, Michael K.C.,Yu, Wensheng,Zawacki, Lisa Guise,Zeng, Qingbei. "II. SAR studies of pyridyl-piperazinyl-piperidine derivatives as CXCR3 chemokine antagonists". scheme or table. p. 1527 - 1531. Retrieved 2011/04/16.
• 2、 -. "NOVEL PYRIDINE COMPOUNDS". Page/Page column 101. . Retrieved 2008/06/13.