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Taking Over Synthesis of "The 6 or 8" - Haverford College Superlab Q2 #461

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AronSchwartzHC opened this Issue Nov 5, 2016 · 11 comments

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AronSchwartzHC commented Nov 5, 2016

Jessica Koshinski I will be taking over "The Synthesis of The 6 and The 8" in Quarter 2 Superlab at Haverford College. The original synthesis is found here [#402]. The previous group [#429] ran into some trouble with the synthesis of 3,5-dichloro-2-methylpyrazine. As a result, we have altered the first step of the synthesis.

We will be recording our work in this lab notebook: "http://malaria.ourexperiment.org/haverford_college_s".

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mattodd Nov 8, 2016

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Hi @AronSchwartzHC - welcome aboard! Could you please take a look at these comments I wrote on another Issue, concerning this "hand-over" phase? Important that we have Issues here that can be closed at some point, and that we're clear which reactions you're going to be doing, and which reactions you're talking about.

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mattodd commented Nov 8, 2016

Hi @AronSchwartzHC - welcome aboard! Could you please take a look at these comments I wrote on another Issue, concerning this "hand-over" phase? Important that we have Issues here that can be closed at some point, and that we're clear which reactions you're going to be doing, and which reactions you're talking about.

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mattodd Nov 16, 2016

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Another quick clarification if you wouldn't mind, @AronSchwartzHC @rbroadrup-HC - is the target here the "6" (which is in the picture) or the "8" (which is in the links) or is it actually both?

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mattodd commented Nov 16, 2016

Another quick clarification if you wouldn't mind, @AronSchwartzHC @rbroadrup-HC - is the target here the "6" (which is in the picture) or the "8" (which is in the links) or is it actually both?

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AronSchwartzHC Nov 16, 2016

@mattodd, @rbroadrup-HC
We are unsure whether it will be the 6 or 8 the depending on the addition of the hydrazine to the dichloro compound. Right now we are only showing the synthesis of the 6 in the picture.

AronSchwartzHC commented Nov 16, 2016

@mattodd, @rbroadrup-HC
We are unsure whether it will be the 6 or 8 the depending on the addition of the hydrazine to the dichloro compound. Right now we are only showing the synthesis of the 6 in the picture.

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mattodd Nov 21, 2016

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Hopefully you got something interesting out of the chlorination reaction you did most recently? Just a note on reaction numbering - can you give each reaction a unique code of the kind I referred to, and use that somewhere in your ELN posts, otherwise we quickly get lost in trying to follow your work. Also, each ELN entry needs a title, so that we can link to it. You'll notice that you can't easily find the URL for your most recent entry because of this...

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mattodd commented Nov 21, 2016

Hopefully you got something interesting out of the chlorination reaction you did most recently? Just a note on reaction numbering - can you give each reaction a unique code of the kind I referred to, and use that somewhere in your ELN posts, otherwise we quickly get lost in trying to follow your work. Also, each ELN entry needs a title, so that we can link to it. You'll notice that you can't easily find the URL for your most recent entry because of this...

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AronSchwartzHC Nov 21, 2016

We are to run the column today. I think I just corrected everything I added the title- a unique code to each of our reactions number and smiles to the ELN entries that are under my name. I will tell Jessica to do the same today.

AronSchwartzHC commented Nov 21, 2016

We are to run the column today. I think I just corrected everything I added the title- a unique code to each of our reactions number and smiles to the ELN entries that are under my name. I will tell Jessica to do the same today.

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AronSchwartzHC Nov 30, 2016

We were unsuccessful in making 3-5-dichloro-2-methylpyrazine. Instead, we are buying it and it should be here at Haverford soon.

AronSchwartzHC commented Nov 30, 2016

We were unsuccessful in making 3-5-dichloro-2-methylpyrazine. Instead, we are buying it and it should be here at Haverford soon.

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mattodd Dec 12, 2016

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Great, @AronSchwartzHC please do keep us posted. Looks good.

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mattodd commented Dec 12, 2016

Great, @AronSchwartzHC please do keep us posted. Looks good.

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AronSchwartzHC Dec 13, 2016

End of Semester report from Aron Schwartz and Jessica Koshinski
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One or both of the molecules above have been synthesized (0.4g). Note that we did buy the 3-5-dichloro-2-methylpyrazine. We also tried the reaction below to see if we would get the amide to add to a specific chlorine as shown below. We will update you on this reaction hopefully this weekend.
image

AronSchwartzHC commented Dec 13, 2016

End of Semester report from Aron Schwartz and Jessica Koshinski
image
image

One or both of the molecules above have been synthesized (0.4g). Note that we did buy the 3-5-dichloro-2-methylpyrazine. We also tried the reaction below to see if we would get the amide to add to a specific chlorine as shown below. We will update you on this reaction hopefully this weekend.
image

@AronSchwartzHC AronSchwartzHC changed the title from Taking Over Synthesis of "The 6 and The 8" - Haverford College Superlab Q2 to Taking Over Synthesis of "The 6 or 8" - Haverford College Superlab Q2 Dec 13, 2016

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AronSchwartzHC Apr 11, 2017

We are having a bit of difficulty with the following reaction. Any ideas would be appreciated.
image
Smiles: ClC1=C(C)N=CC2=NN=C(C3=CC=C(OC(F)F)C=C3)N21

The reaction was run at room temperature with equal molar equivalents of reagent to ring closing agent.
The reaction was then run a second time at higher temperature (35˚C) and a 3:1 molar ratio of ring closing agent to starting material.
Protocols can be see here: http://malaria.ourexperiment.org/haverford_college_s References to (HASJK-2-10) and (HASJK-2-11).

What about running the reaction in toluene at higher temperature?

Thanks,
Aron

AronSchwartzHC commented Apr 11, 2017

We are having a bit of difficulty with the following reaction. Any ideas would be appreciated.
image
Smiles: ClC1=C(C)N=CC2=NN=C(C3=CC=C(OC(F)F)C=C3)N21

The reaction was run at room temperature with equal molar equivalents of reagent to ring closing agent.
The reaction was then run a second time at higher temperature (35˚C) and a 3:1 molar ratio of ring closing agent to starting material.
Protocols can be see here: http://malaria.ourexperiment.org/haverford_college_s References to (HASJK-2-10) and (HASJK-2-11).

What about running the reaction in toluene at higher temperature?

Thanks,
Aron

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@AronSchwartzHC From what I could see in the 1H NMR of the product from your experiment HASJK-2-9, it appears that you did not isolate the product hydrazone. I suggest that you re-inspect the identity of your starting material prior to modifying the ring closure reaction conditions.

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MedChemProf commented Apr 11, 2017

@AronSchwartzHC From what I could see in the 1H NMR of the product from your experiment HASJK-2-9, it appears that you did not isolate the product hydrazone. I suggest that you re-inspect the identity of your starting material prior to modifying the ring closure reaction conditions.

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AronSchwartzHC Jun 26, 2017

Haverford College will not continue with the synthesis of the 6 or the 8. The starting material, 3,5-dichloro-2-methylpyrazine, is too expensive to repurchase.

AronSchwartzHC commented Jun 26, 2017

Haverford College will not continue with the synthesis of the 6 or the 8. The starting material, 3,5-dichloro-2-methylpyrazine, is too expensive to repurchase.

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