N-[2-Chloro-3-formyl-4-pyridinyl]carbamic acid tert-butyl ester

Base Information

• Chemical Name: N-[2-Chloro-3-formyl-4-pyridinyl]carbamic acid tert-butyl ester
• CAS No.: 893423-62-6
• Molecular Formula: C11H13ClN2O3
• Molecular Weight: 256.689
• Hs Code.: 2933399090
• Mol file: 893423-62-6.mol

Synonyms:carbamic acid, N-(2-chloro-3-formyl-4-pyridinyl)-, 1,1-dimethylethyl ester;

Chemical Property of N-[2-Chloro-3-formyl-4-pyridinyl]carbamic acid tert-butyl ester

Chemical Property:

• Boiling Point: 332.332 °C at 760 mmHg
• PKA: 11.46±0.70(Predicted)
• Flash Point: 154.789 °C
• PSA: 68.29000
• Density: 1.314 g/cm³
• LogP: 2.96750
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C

Purity/Quality:

98%min ^*data from raw suppliers

4-(Boc-amino)-2-chloro-3-pyridinecarbaldehyde ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 4-(Boc-amino)-2-chloro-3-pyridinecarbaldehyde is used as a reagent in the synthesis of naphthyridinones as allosteric dual Akt1 and Akt2 inhibitors.

Technology Process of N-[2-Chloro-3-formyl-4-pyridinyl]carbamic acid tert-butyl ester

There total 8 articles about N-[2-Chloro-3-formyl-4-pyridinyl]carbamic acid tert-butyl ester 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%

(2-chloro-pyridin-4-yl)-carbamic acid tert-butyl ester (234108-73-7) + N,N-dimethyl-formamide (68-12-2,33513-42-7) → tert-butyl (2-chloro-3-formylpyridin-4-yl)carbamate (893423-62-6)

Guidance literature:

tert-butyl 2-chloropyridin-4-ylcarbamate; With lithium tert-butyl; In tetrahydrofuran; n-Pentane; at -70 ℃; for 2h; Inert atmosphere;

N,N-dimethyl-formamide; In tetrahydrofuran; n-Pentane; at -70 - 20 ℃; for 3h; Inert atmosphere;

DOI:10.1016/j.bmcl.2008.04.074

Reference yield:

N,N-dimethyl-formamide (68-12-2,33513-42-7) → tert-butyl (2-chloro-3-formylpyridin-4-yl)carbamate (893423-62-6)

Guidance literature:

(2-chloro-pyridin-4-yl)-carbamic acid tert-butyl ester; With tert.-butyl lithium; In tetrahydrofuran; at -78 ℃; for 2h;

N,N-dimethyl-formamide; In tetrahydrofuran; at 20 ℃; for 3h;

Reference yield:

C10H12ClLiN2O2 + N,N-dimethyl-formamide (68-12-2,33513-42-7) → tert-butyl (2-chloro-3-formylpyridin-4-yl)carbamate (893423-62-6)

Guidance literature:

In tetrahydrofuran; pentane; at -78 - 20 ℃; for 3h; Product distribution / selectivity;

upstream raw materials:

N,N-dimethyl-formamide

(2-chloro-pyridin-4-yl)-carbamic acid tert-butyl ester

tert.-butyl lithium

4-Amino-2-chloropyridine

Downstream raw materials:

2-[4-(1,3-dioxolan-2-yl)phenyl]-5-methoxy-3-phenyl-1,6-naphthyridine

5-hydrazino-3-phenyl-2-(4-{[4-(5-pyrazin-2-yl-4H-1,2,4-triazol-3-yl)piperidin-1-yl]methyl}phenyl)-1,6-naphthyridine

(3-phenyl-2-{4-[4-(5-pyridin-2-yl-4H-[1,2,4]triazol-3-yl)-piperidin-1-ylmethyl]-phenyl}-[1,6]naphthyridin-5-yl)-hydrazine

5-hydrazino-3-phenyl-2-(4-{[4-(5-pyridin-2-yl-1H-1,2,4-triazol-3-yl)piperidin-1-yl]methyl}phenyl)-1,6-naphthyridine

Refernces

• 1、 Uhlenbrock, Niklas,Smith, Steven,Weisner, J?rn,Landel, Ina,Lindemann, Marius,Le, Thien Anh,Hardick, Julia,Gontla, Rajesh,Scheinpflug, Rebekka,Czodrowski, Paul,Janning, Petra,Depta, Laura,Quambusch, Lena,Müller, Matthias P.,Engels, Bernd,Rauh, Daniel. "Structural and chemical insights into the covalent-allosteric inhibition of the protein kinase Akt". . p. 3573 - 3585. Retrieved 2019/03/28.
• 2、 Siu, Tony,Liang, Jun,Arruda, Jeannie,Li, Yiwei,Jones, Raymond E.,Defeo-Jones, Deborah,Barnett, Stanley F.,Robinson, Ronald G.. "Discovery of potent and cell-active allosteric dual Akt 1 and 2 inhibitors". scheme or table. p. 4186 - 4190. Retrieved 2009/04/07.