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21st January 2013 @ 23:12
Mnr: MNR81-90

Synthesis of near neighbour analog MNR82-1 from pyrrole AEW45-1 and thiazolidinone PMY13-1

 

Hazard Assessment

HIRAC MNR82.pdf

Procedure

Thiazolidinone PMY13-1 (0.078 g, 0.41 mmol) was dissolved in ethanol (6 mL) and piperdine (0.06 mL, 0.61 mmol) was added. AEW45-1 (100 mg, 0.41 mmol) was added to the mixture, and the resulting solution was heated to 60 °C. After 5 hours, TLC showed consumption of AEW45-1 and a precipitate had formed.  The reaction was allowed to cool to room temperature, was filtered and the precipitate washed with EtOH to yield a dark orange solid (0.117 g, 0.28 mmol, 68%)

TLC 

SANY0049.JPG

TLC after 5 hours, 50% EtOAc/Hex

NMR

mnr82-1_1H.pdf
mnr82-1.zip

Product not soluble in CDCl3, weak sample in DMSO, hard to tell but onlt very slight traces of aldehyde therefore suggesting product.

Conclusion

 Further purification required, perhaps HPLC or washing with another organic solvent?

HPLC


It was found while trying to prepare a sample for analytical HPLC that the product was not fully soluble in MeCN, water or a mixture of both.

SANY0053.JPG
SANY0055.JPG

Same vial after shaking then after standing for 1 hour

MNR82-1 (3 mg) in MeCN/water (1.7 mL)

 

Strings

Starting Materials

InChI=1S/C13H12N2O3/c1-9-7-11(8-16)10(2)14(9)12-3-5-13(6-4-12)15(17)18/h3-8H,1-2H3

InChI=1S/C10H9NOS/c12-9-7-13-10(11-9)6-8-4-2-1-3-5-8/h1-6H,7H2,(H,11,12)/b10-6-

 

Product

InChI=1S/C23H19N3O3S/c1-15-12-18(16(2)25(15)19-8-10-20(11-9-19)26(28)29)14-21-23(27)24-22(30-21)13-17-6-4-3-5-7-17/h3-14H,1-2H3,(H,24,27)/b21-14-,22-13-

 

Linked Posts
Attached Files
MNR82-1_table.PNG
MNR82_scheme.png
HIRAC MNR82.pdf
mnr82-1_1H.pdf
mnr82-1.zip
SANY0053.JPG
SANY0055.JPG
Comments
Re: Synthesis of Near Neighbour Analog MNR82-1 by OSDD Malaria
26th January 2014 @ 22:33
OSM-S-109
Note structure of product wrong in reaction scheme above - missing nitrogen