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20th November 2014 @ 15:03

Reaction Scheme: 


Experimental Procedure: 

 see Synthesis of (E)-4-((2-(6-chloropyridin-2-yl)hydrazono)methyl)benzonitrile (JS 10-1) 

To a solution of JS 10-1 (100 mg, 0.39 mmol, crude) stirred in CH2Cl(5.5 mL) was added Iodosobenzene diacetate (138.5 mg, 0.43 mmol). The reaction was stirred at room temperature 

Risk Assessment :

 

JS 8-1.docx

SMILES 

ClC1=CC=CC(N/N=C/C2=CC=C(C#N)C=C2)=N1

to

ClC1=CC=CC2=NN=C(C3=CC=C(C#N)C=C3)N21

 

InchI Strings

InChI=1S/C13H9ClN4/c14-12-2-1-3-13(17-12)18-16-9-11-6-4-10(8-15)5-7-11/h1-7,9H,(H,17,18)/b16-9+

to

InChI=1S/C13H7ClN4/c14-11-2-1-3-12-16-17-13(18(11)12)10-6-4-9(8-15)5-7-10/h1-7H

20th November 2014 @ 11:34

Note: See Synthesis of (E)-4-((2-(6-chloropyridin-2-yl)hydrazono)methyl)benzonitrile (JS 6-1) for previous problems trying to synthesise the desired E isomer . 


Reaction Scheme 

Experimental Procedure 

JS 4-1 [see - Synthesis of 2-chloro-6-hydrazinylpyradine (JS 4-1) ] (1.005 g, 7 mmol) was stirred into a solution of ethanol (100 mL). 4-cyanobenzaldehyde (0.92 g, 7 mmol) was added and the reaction was stirred at refux for 2 hours.

Risk Assessment 

JS 10-1.docx

SMILES 

 

ClC1=CC=CC(NN)=N1 

and

[H]C(C1=CC=C(C#N)C=C1)=O

to

ClC1=CC=CC(N/N=C/C2=CC=C(C#N)C=C2)=N1

 

InChI Strings 

InChI=1S/C5H6ClN3/c6-4-2-1-3-5(8-4)9-7/h1-3H,7H2,(H,8,9)

and

InChI=1S/C8H5NO/c9-5-7-1-3-8(6-10)4-2-7/h1-4,6H

to

InChI=1S/C13H9ClN4/c14-12-2-1-3-13(17-12)18-16-9-11-6-4-10(8-15)5-7-11/h1-7,9H,(H,17,18)/b16-9+


Linked Posts
Attached Files
19th November 2014 @ 06:17

19 November 2014 @ 16:51

Synthesis of SGS 4-1 (AEW 198-1)

http://malaria.ourexperiment.org/triazolopyrazine_se/11058/Synthesis_of_E2chloro62pyridin2ylmethylenehydrazinylpyrazine_AEW_1982.html

Reaction performed by Jason Chami and Mackenzie Shaw.

SGS 1-1 (1.06 g, 7.33 mmol) was stirred into MeCN (15 mL). 2-Pyridinecarboxaldehyde (0.77 g, 7.2 mmol) and AcOH (0.4 mL) were added to the mixture.  This reaction mixture was then stirred at room temperature overnight.

 Synthesis of SGS 4-1

SMILES

ClC1=CN=CC(NN)=N1

and

O=C([H])C1=CC=CC=N1

to

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

 

InchI Strings

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

and

InChI=1S/C6H5NO/c8-5-6-3-1-2-4-7-6/h1-5H

to


InChI=S/C10H8ClN5/c11-9-6-12-7-10(15-9)16-14-5-8-3-1-2-4-13-8/h1-7H,(H,15,16)/b14-5+

15th November 2014 @ 13:45

Reaction Scheme: 


Experimental Procedure: 

 see Synthesis of (E)-4-((2-(6-chloropyridin-2-yl)hydrazono)methyl)benzonitrile (JS 6-1) 

To a solution of JS 6-1 (100 mg, 0.39 mmol, crude) stirred in dry THF (8 mL) was added chloramine-T (97.8 mg, 0.43 mmol). The reaction was stirred at room temperature over the weekend. 

No change in TLC. The solvent was removed in vacuo and then the solid re-dissolved in 2-MeTHF. This was refluxed overnight to no avail. The reaction has not proceeded at all due to the possibility that the starting material is the incorrect isomer (the Z isomer). 

 

Risk Assessment :

JS 9-1.docx

SMILES 

ClC1=CC=CC(N/N=C/C2=CC=C(C#N)C=C2)=N1

to

ClC1=CC=CC2=NN=C(C3=CC=C(C#N)C=C3)N21

 

InchI Strings

InChI=1S/C13H9ClN4/c14-12-2-1-3-13(17-12)18-16-9-11-6-4-10(8-15)5-7-11/h1-7,9H,(H,17,18)/b16-9+

to

InChI=1S/C13H7ClN4/c14-11-2-1-3-12-16-17-13(18(11)12)10-6-4-9(8-15)5-7-10/h1-7H

Attached Files
15th November 2014 @ 13:40

Optimising Reaction conditions to avoid side product synthesis 


Reaction Scheme 


Experimental Procedure 

Compound 3 (0.1 g, ) was treated with  Hydrazine hydrate - 64 % weight in H2O - (0.019 mL, 10 equivs) in EtOH (1.2 ml) . The resulting mixture was stirred overnight at reflux. TLC of the resulting mixture in two different solvent systems will be performed performed (100% EtOAc and 10/90 EtOAc/Hexane). After 24 hours The TLC indicted the reaction was not complete . TLC after 48 hours showed the reaction was still not complete but more product had formed.  An NMR was taken at this stage and showed the product was  present in a ratio of 2:1 with the starting material.These conditions favour synthesis of the product faster than conditions in (JS 5-5). 

RISK ASSESSMENT 

JS 5-2.docx

InChI strings

InChI=1S/C12H8Cl2N2O/c13-8-3-1-4-9(7-8)15-12(17)10-5-2-6-11(14)16-10/h1-7H,(H,15,17)

to

InChI=1S/C12H11ClN4O/c13-8-3-1-4-9(7-8)15-12(18)10-5-2-6-11(16-10)17-14/h1-7H,14H2,(H,15,18)(H,16,17)

SMILES

ClC1=NC(C(NC2=CC=CC(Cl)=C2)=O)=CC=C1

to

O=C(NC1=CC=CC(Cl)=C1)C2=CC=CC(NN)=N2