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16th August 2013 @ 01:35

Synthesised using direct method but also see Hydrolysis of acyl-iminothiazolidinone PMY 14-1 (PMY 16-1) for reference.

(PMY 13-1) (135 mg, 0.70 mmol, 1.02 equiv.) was dissolved in ethanol (10 mL) and combined with piperidine (0.11 mL, 1.11 mmol, 1.61 equiv.). AEW 2-3 (150 mg, 0.627 mmol, 1.00 equiv.) was dissolved in ethanol (5 mL) and added to the mixture, and the resulting clear brown solution was heated to 60 °C for 2.5 h 


Data

AEW 80-1 check.zip
AEW 80-1.pdf

Hazard and Risk Assessment:

See Synthesis of (2Z,5Z)-5-((2,5-dimethyl-1-(p-tolyl)-1H-pyrrol-3-yl)methylene)-2-(phenylimino)thiazolidin-4-one (AEW 76-1, OSM-S-37)

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16th August 2013 @ 01:12

For original synthesis see here. Resynthesised for characterisation and possible submission to new assay.

Going to start at 4.30pm

AEW 76-1 (50 mg, 0.13 mmol, 1 equiv.) was dissolved partially in toluene (~5 mL) and stirred under a nitrogen atmosphere. Pyridine (~20 μL, 0.25 mmol, 1.9 equiv.) was added, followed by acetic anhydride (~40 μL, 0.4 mmol, 3 equiv.). The mixture was heated to 80 °C and left stirring overnight under nitrogen.

Hazard and Risk Assesment:

See Acetylation of para-trifluoromethyl near neighbour analogue (ZYH 12-1)

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13th August 2013 @ 08:02

Resynthesis of OSM-S-37, See ZYH 5-1 for original expt.

2-phenyliminothiazolidin-4-one (PMY 13-1) (123 mg, 0.640 mmol, 1.02 equiv.) was dissolved in ethanol (10 mL) and combined with piperidine (0.100 mL, 1.01 mmol, 1.61 equiv.). 2,5-dimethyl-1-(4-methylphenyl)-1H-pyrrole-3-carboxaldehyde (LMW 5-1) (145 mg, 0.627 mmol, 1.00 equiv.) was dissolved in ethanol (5 mL) and added to the mixture, and the resulting clear brown solution was heated to 60 °C for 2.5 h then removed from the heat and stirred at room temperature o/n. Reaction mixture cooled and stirred in an ice bath and then filtered to yield a yellow solid. First filtration, solid passed through and blocked sinter. Re-filtered using fine grade filter paper to give a bright yellow solid that was dried at the high vac (x mg). Sinter funnel washed with EtOAc and the illuminous yellow mother liquors were concentrated to yield

Hazard and Risk Assessment:

See Synthesis of p-methyl arylpyrrole based near neighbour (ZYH 5-1)

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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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30th January 2013 @ 07:11
Mnr: MNR91-100

Synthesis of near neighbour analog MNR91-1 from pyrrole AEW50-1 and thiazolidinone MNR70-2

 

Hazard Assessment

HIRAC MNR82.pdf

Procedure

Thiazolidinone MNR70-2 (0.072 g, 0.35 mmol) was dissolved in ethanol (5 mL) and piperdine (0.05 mL, 0.52 mmol) was added. AEW50-1 (0.070 g, 0.35 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 but no precipitate formed.  THe reaction mixture was concentrated then dissolved in DCM (5 mL) and washed with water (5 mL).  The water was then washed with DCM (5 mL x 2), the organic layers were combined, dried over magnesium sulphate, filtered and concentrated to give the crude as brown oil (0.104 g).

NMR

 NMR of the crude extraction:- 

mnr91-1_crude_1H.pdf
mnr91-1_extract.zip

 

Potential signs of the product but this needs cleaned up

Column

only resulted in a mess

mnr91-1_frac22-34_1H.pdf

Conclusion


No clean product recovered, reaction not taken any further.  This needs repeated.

 

Strings

Starting Materials

InChI=1S/C12H12N2O/c1-9-7-11(8-15)10(2)14(9)12-5-3-4-6-13-12/h3-8H,1-2H3

 InChI=1S/C10H9NO2S/c12-8-3-1-2-7(4-8)5-10-11-9(13)6-14-10/h1-5,12H,6H2,(H,11,13)/b10-5-

 

Product

InChI=1S/C22H19N3O2S/c1-14-10-17(15(2)25(14)20-8-3-4-9-23-20)13-19-22(27)24-21(28-19)12-16-6-5-7-18(26)11-16/h3-13,26H,1-2H3,(H,24,27)/b19-13-,21-12-

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