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09-06-2016, First step in synthesis of the hetero-oxadiazole, reaction of 2-6 dichloropyrazine with malononitrile, following procedure from Nikishkin et al (2013)
09-11-2016, Work up of the second attempt at step 1
09-23-2016. Step 1 redo, on 5 gram scale
09-24-2016. Work up of 09-23-2016
09-29-2016, work up and purification of [4]
09/28/2016 Step 4, on a larger scale this time. Conversion of methyl 6-chloropyrazine-2-carboxylate [3] to methyl 6-hydrazineylpyrazine-2-carboxylate [4] using hydrazine according to AEW 85-5
10/07/2016 GC mass spec characterization of rxn from [4]->[5]
10/18/16: Trial work up of reaction of 6-chloropyrazinecarbonitrile and hydrazine
10/4/16: Trial of Step 4:Product [4] to Product [5]
10/6/16: Trial Synthesis of 6-hydrazinelypyrazine-2-carbonitrile and from 6- hydrazinelypyrazine-2-carboximidhydrazide from chloropyrazinecarbonitrile
9/12/16 Step 2 in synthesis. Going from [2]->[3]
9/13/16: Work-up of product [3] and TLC plates
9/15/16: Second Synthesis of Methyl 6-chloropyrazine-2-carboxylate [product 3]
9/18/16-9/20/16: Trial Synthesis of Methyl 6-hydrazineylpyrazine-2-carboxylate (Product 4)
9/22/16: Inconclusive Trial Synthesis of Methyl 6-hydrazineylpyrazine-2-carboxylate (Product 4)
9/25/16-9/27/16: Synthesis of Product 3, methyl 6-chloropyrazine-2-carboxylate
9/27/2016 Late Night
9/29/2016 HNMR of product 4, and HNMR of product 4 after D2O exchange 01/10/2016
9/8/16-Continued Synthesis of 2-(6-chloropyrazin-2(1H)-ylidene)malononitrile
CNMR so far
HNMR so far, of all relevant compounds
The Synthetic scheme of Hetero-oxadiazole Synthesis
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26th September 2016 @ 01:59

reaction scheme3-4.png

Based on: http://malaria.ourexperiment.org/triazolopyrazine_se/11581/Synthesis_of_2Chloro6hydrazinylpyrazine_AEW_855.html).

The product of the hydrazine reaction from 9/18/16 was partitioned in 10 mL H2O and 10 mL EtOAc. The organic layer was removed, and the aqueous layer was extracted 3 times with EtOAc. The organic layers were washed with brine and dried with MgSO4. TLC showed product in both the organic layer and the aqueous layer (eluent: 3:1 EtOAc to Hexane). In the image, the plate on the left is spotted (from left to right) with product 3, a co-spot, and the organic layer from the hydrazine reaction. The plate on the right is spotted with product 3, a co-spot, and the aqueous layer from the hydrazine reaction. Once the volatiles were removed from the organic layer, there was a slightly yellow product present. However, there was not enough product left to characterize. The goal is to start the synthesis over and scale it up, so when we get to this step again, we will be able to determine if it worked.

Attached Files
reaction scheme3-4.png
organic and aqueous tlc.png