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11th April 2013 @ 06:41
Mnr: MNR121-130

 Starting material from Synthesis of Near Neighbour Analog MNR82-2 

also Synthesis of Near Neighbour Analog MNR82-1

Procedure as for Example 6 step b

Hazard Assessment

HIRAC MNR82.pdf

Procedure

To MNR82-2 (0.040 g, 0.1 mmol) in MeOH (2.4 mL) and DMF (0.6 mL) was added a catalytic amount of Palladium on charcoal (10%) and the reaction was stirred under an atmosphere of hydrogen overnight.  The reaction was then filtered through celite and concentrated.  Crude NMR showed DMF was still present but the crude mixture was soluble in CDCl3.  

Crude NMR

mnr121-1_filter_CDCl3_1H.pdf
mnr121-1_filter_CDCl3.zip

Colum 5% MeOH/CHCl3

2013-04-12 15.42.04.jpg

 

Frac 9 -  as a yellow oil, upon adding DCM a solid formed.  DCM removed and dried.

 

Frac 10-17 -

NMR

 

Conclusion

 

Strings

Starting Materials

InChI=1S/C22H18N4O3S/c1-14-12-16(15(2)25(14)18-8-10-19(11-9-18)26(28)29)13-20-21(27)24-22(30-20)23-17-6-4-3-5-7-17/h3-13H,1-2H3,(H,23,24,27)/b20-13-

Product

InChI=1S/C22H20N4OS/c1-14-12-16(15(2)26(14)19-10-8-17(23)9-11-19)13-20-21(27)25-22(28-20)24-18-6-4-3-5-7-18/h3-13H,23H2,1-2H3,(H,24,25,27)/b20-13-

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25th March 2013 @ 04:15
Mnr: MNR81-90

Synthesis of near neighbour analog MNR82-2 from pyrrole AEW45-1 and thiazolidinone PMY13-1

As for - Synthesis of Near Neighbour Analog MNR82-1

Starting materials from - Synthesis of 2,5-dimethyl-1-(4-nitrophenyl)-1H-pyrrole-3-carbaldehyde (AEW 45-1)

Preparation of 2-phenyliminothiazolidin-4-one (PMY 13-1)

 

Hazard Assessment

HIRAC MNR82.pdf

Procedure

Thiazolidinone PMY13-1 (0.094 g, 0.49 mmol) was dissolved in ethanol (7 mL) and piperdine (0.07 mL, 0.74 mmol) was added. AEW45-1 (120 mg, 0.49 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 (0.147 g, 0.35 mmol, 72 %)

NMR

mnr82-2_1H.pdf
mnr82-2_filter.zip

Conclusion

 Similr result to before s taken on to the next step, the reduction of the nitro group.

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/C22H18N4O3S/c1-14-12-16(15(2)25(14)18-8-10-19(11-9-18)26(28)29)13-20-21(27)24-22(30-20)23-17-6-4-3-5-7-17/h3-13H,1-2H3,(H,23,24,27)/b20-13-

 

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28th February 2013 @ 06:49
Mnr: MNR101-110

Starting material from AEW45-1

Hazard Assement

HIRAC MNR102.pdf

Procedure

To a mixture of AEW45-1 (75 mg, 0.31 mmol) in methanol (2 mL) under argon was added Pd/C (20 mg).  The flask was then flushed with hydrogen gas three times and left to stir overnight at room temperature.  TLC in the morning showed consumption of starting material but 4 new spots.  The mixture was filtered through celite which was then rinsed with MeOH and concentrated to give the the crude (15 mg).  The celite was then washed with DMF (20 mL) and concentrated at 70 °C / 55 mbar for 2 hours.  Ice was then added to this crude mixture containing some DMF (1-2 mL) and what looked like some solid started to form.  DCM and water was added to the flask and a solid formed at the interface.  This was filered and dried to yeils a pale brown solid (24 mg).


The filtrate was extracted but the organic layer contained mostly DMF.


NMR

mnr102-1_filter.zip

mnr102-1_filtrate.zip


Conclusion

Unsuccesful reaction.  The NMR of the filtered solid shows many Me peaks and more than one pyrrole H.  There looks to be a solubility problem with this procedure with the SM and product(s). 

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31st January 2013 @ 07:31
Mnr: MNR91-100

Synthesis of near neighbour analog MNR95-1 from pyrrole AEW49-1 and thiazolidinone MNR88-1.

 InChI=1S/C22H19N3O2S/c1-14-12-16(15(2)25(14)18-6-4-3-5-7-18)13-20-21(27)24-22(28-20)23-17-8-10-19(26)11-9-17/h3-13,26H,1-2H3,(H,23,24,27)/b20-13-

 

Hazard Assessment

HIRAC MNR82.pdf

Procedure

Thiazolidinone MNR88-1 (0.08 g, 0.4 mmol) was dissolved in ethanol (6 mL) and piperdine (0.06 mL, 0.6 mmol) was added.  AEW49-1 (0.080 g, 0.4 mmol) was added to the mixture, and the resulting solution was heated to 60 °C overnight.  The reaction was then allowed to cool to room temperature and the precipitate was filtered and washed with EtOH to give an orange solid (0.125 g, 0.32 mmol, 80%)

NMR

 

mnr95-1_1H.pdf
mnr95-1.zip

Conclusion

 Proton NMR looks good and sample is ready to send for testing, further characterisation still needed.

Strings

Starting Materials

InChI=1S/C13H13NO/c1-10-8-12(9-15)11(2)14(10)13-6-4-3-5-7-13/h3-9H,1-2H3

InChI=1S/C9H8N2O2S/c12-7-3-1-6(2-4-7)10-9-11-8(13)5-14-9/h1-4,12H,5H2,(H,10,11,13)

Product

InChI=1S/C22H19N3O2S/c1-14-12-16(15(2)25(14)18-6-4-3-5-7-18)13-20-21(27)24-22(28-20)23-17-8-10-19(26)11-9-17/h3-13,26H,1-2H3,(H,23,24,27)/b20-13-

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31st January 2013 @ 07:27
Mnr: MNR91-100

Synthesis of near neighbour analog MNR94-1 from pyrrole AEW49-1 and thiazolidinone MNR70-2.

 

 

Hazard Assessment

HIRAC MNR82.pdf

Procedure

Thiazolidinone  MNR70-2 (0.08 g, 0.4 mmol) was dissolved in ethanol (6 mL) and piperdine (0.06 mL, 0.6 mmol) was added.  AEW49-1 (0.080 g, 0.4 mmol) was added to the mixture, and the resulting solution was heated to 60 °C overnight. The reaction was then allowed to cool to room temperature and the precipitate was filtered and washed with EtOH to give a dark yellow solid (0.124 g, 0.32 mmol, 79%)

NMR

 

mnr94-1_1H.pdf
mnr94-1.zip

Conclusion

 Proton NMR looks good and sample is ready to send for testing, further characterisation still needed.

Strings

Starting Materials

InChI=1S/C13H13NO/c1-10-8-12(9-15)11(2)14(10)13-6-4-3-5-7-13/h3-9H,1-2H3

InChI=1S/C9H8N2O2S/c12-7-3-1-2-6(4-7)10-9-11-8(13)5-14-9/h1-4,12H,5H2,(H,10,11,13)

Product

InChI=1S/C22H19N3O2S/c1-14-11-16(15(2)25(14)18-8-4-3-5-9-18)12-20-21(27)24-22(28-20)23-17-7-6-10-19(26)13-17/h3-13,26H,1-2H3,(H,23,24,27)/b20-12-

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