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4th August 2015 @ 10:01

Summary



A synthesis was performed to create a novel antimalarial which can test the properties of Naphthalene functional group. The molecule will be cyclised to form a triazolopyrazine core.

 

Reagents

Method

2-chloro-6-hydrazinylpyrazine (4.00 g, 27.67 mol, 1 equiv) was added to a 250 mL round bottomed flask with a magnetic stirrer. 160 ml of Ethanol was added as a solvent, NOTE: this was not a sufficient amount for the 4.00 g of 2-chloro-6-hydrazinylpyrazine. However due to the small flask size no more could be added. 

2-napthaldehyde (4.32 g, 27.67 mol, 1 equiv) was then added, colour change indicated reaction completion so sample was analysed via TLC analysis using 1:1 petroleum to ethyl acetate. UV light revealed the sample.

The completed reaction mixture was dried in a rotary evaporator at low pressure before being placed in vials for further synthesis and analysis.

Data

TLC

 

TLC TY2-1.png

TLC of 2-chloro-6-hydrazinylpyrazine, product and 2-chloro-6-hydrazinylpyrazine and just the product

TLC 2 TY2-1.jpg

 Same TLC plate as above

Dried Product ( 7.28 g, 25.75 mmol, 93% yield).

 

InChI Strings

InChI=1S/C4H5ClN4/c5-3-1-7-2-4(8-3)9-6/h1-2H,6H2,(H,8,9)

AND

InChI=1S/C11H8O/c12-8-9-5-6-10-3-1-2-4-11(10)7-9/h1-8H

TO

InChI=1S/C15H11ClN4/c16-14-9-17-10-15(19-14)20-18-8-11-5-6-12-3-1-2-4-13(12)7-11/h1-10H,(H,19,20)/b18-8+

SMILES

ClC1=CN=CC(NN)=N1

AND

O=C([H])C1=CC=C(C=CC=C2)C2=C1

TO

ClC1=CN=CC(N/N=C/C2=CC=C(C=CC=C3)C3=C2)=N1

 This reaction is the first in the process towards a final potential antimalarial - https://github.com/OpenSourceMalaria/OSM_To_Do_List/issues/338

 

Attached Files
(E)-2-chloro-6-(2-(naphthalen-2-ylmethylene)hydrazinyl)pyrazine.png
TY2-1 Chemical Reagents.png
HIRAC TY2-1.pdf
Tom OSM 2-1.cdxml
TLC TY2-1.png
TLC 2 TY2-1.jpg