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11th May 2017 @ 07:28

 

Crude AEW 272-2 (6.12 g, 20.3 mmol, 1 equiv.) was dissolved in anhdrous CH­2Cl2 (203 mL) and (diacetoxyiodo)benzene (6.60 g, 20.3 mmol, 1 equiv.) was added. The reaction mixture was stirred at rt for 3 h and then quenched by the addition of a saturated aqueous solution of sodium hydrogen carbonate. Aqueous layers were separated and then extracted with CH­2Cl2 and then organic layers were combined and washed with brine (× 1), dried (MgSO4), filtered and evaporated. The crude mixture was then purified by

NMR

 

Hazard and Risk Assesment:


Strings:


InChI=1S/C11H7Cl3N4/c12-8-2-1-7(3-9(8)13)4-16-18-11-6-15-5-10(14)17-11/h1-6H,(H,17,18)/b16-4+

to

InChI=1S/C11H5Cl3N4/c12-7-2-1-6(3-8(7)13)11-17-16-10-5-15-4-9(14)18(10)11/h1-5H

ClC1=CN=CC(N/N=C/C2=CC(Cl)=C(Cl)C=C2)=N1

to

ClC1=CN=CC2=NN=C(C3=CC(Cl)=C(Cl)C=C3)N21

11th May 2017 @ 05:12

Repeat of Synthesis of 2-Chloro-6-hydrazinylpyrazine (AEW 85-1), see also Synthesis of 2-Chloro-6-hydrazinylpyrazine (AEW 85-2) and Synthesis of 2-Chloro-6-hydrazinylpyrazine (AEW 85-3)

 

2,6-dichloropyrazine (21 g, 141 mmol, 1 eq) was dissolved in EtOH (282 mL, 0.50 M), and hydrazine hydrate (13.5 mL, 270 mmol, 2 eq) added. The reaction mixture was stirred at reflux for 8 hours.

The solvent was removed under reduced pressure to give a pale yellow solid. Water (~150 mL) and EtOAc (~200 mL) were added, and the mixture was shaken in an attempt to dissolve all solid. The organic layer was removed, the aqueous layer extracted with EtOAc (3 x 100 mL), and the combined organic layers washed with brine (~30 mL) before being concentrated under reduced pressure to yield a yellow solid 

Data:

Crude 300 MHz Data:

AEW 85.pdf
AEW 85.zip

Hazard and Risk Assessment:

See Synthesis of 2-Chloro-6-hydrazinylpyrazine (AEW 85-1)

InChi Strings:

InChI=1S/C4H2Cl2N2/c5-3-1-7-2-4(6)8-3/h1-2H

to

InChI=1S/C4H5ClN4/c5-3-1-7-2-4(8-3)9-6/h1-2H,6H2,(H,8,9)

Linked Entries
11th May 2017 @ 05:06

Apologies this lab experiment was performed on Thurs/Fri 4/5th May

Outcome:

Obtained the desired product in quantitative yields. NMR Spectra to be uploaded asap.

Reason for Experiment: Synthesised for SSP Class 2017

 

Scheme:

 

Procedure:


AEW 85 (5.00 g, 34.6 mmol, 1.00 equiv.) was dissolved in EtOH (346 mL) and then 4-chlorobenzaldehyde (4.86 g, 34.6 mmol, 1.00 equiv.) was added. The brown/orange soln. was stirred for ten minutes at room temperature. A pale brown solid crashed out of the reaction mixture. The reaction was stirred for a further 2 h and then progress monitored by TLC (10% EtOAc in Hexane) - reaction complete.

Solid filtered under vacuum to give a pale yellow solid 9.8 g, that was dried at the high vac to yield a pale beige/brown powder in quantitative yield. Used as crude in following SSP reactions without NMR evaluation

Hazard and Risk Assessment:

HIRAC SSP OSDD Prac 1 2016.doc

Data:

TLC at 40 min (10% EtoAc in Hexane)

AEW 273-1 (10% EtoAc in Hex).JPG

NMR

Strings:

ClC1=CN=CC(N/N=C/C2=CC=C(Cl)C=C2)=N1

to

ClC1=CN=CC2=NN=C(C3=CC=C(Cl)C=C3)N21

 

InChI=1S/C11H8Cl2N4/c12-9-3-1-8(2-4-9)5-15-17-11-7-14-6-10(13)16-11/h1-7H,(H,16,17)/b15-5+

to

InChI=1S/C11H6Cl2N4/c12-8-3-1-7(2-4-8)11-16-15-10-6-14-5-9(13)17(10)11/h1-6H

11th May 2017 @ 04:49

Apologies this lab experiment was performed on Thurs/Fri 4/5th May

Outcome:

Obtained the desired product in quantitative yields. NMR Spectra to be uploaded asap.

Reason for Experiment: Synthesised for SSP Class 2017

 

Scheme:

 

Procedure:


AEW 85 (5.00 g, 34.6 mmol, 1.00 equiv.) was dissolved in EtOH (346 mL) and then 2,4-dichlorobenzaldehyde (6.05 g, 34.6 mmol, 1.00 equiv.) was added. The brown/orange soln. was stirred for ten minutes at room temperature. A pale brown solid crashed out of the reaction mixture. The reaction was stirred for a further 2 h and then progress monitored by TLC (10% EtOAc in Hexane) - reaction complete.

Solid filtered under vacuum to give a pale brown solid 11.2 g, that was dried at the high vac to yield a pale beige/brown powder in quantitative yield. Used as crude in following SSP reactions without NMR evaluation

Hazard and Risk Assessment:

HIRAC SSP OSDD Prac 1 2016.doc

Data:

TLC at 40 min (10% EtoAc in Hexane)

AEW 273-1 (10% EtoAc in Hex).JPG

NMR

Strings:

InChI=1S/C4H5ClN4/c5-3-1-7-2-4(8-3)9-6/h1-2H,6H2,(H,8,9)

and

InChI=1S/C7H4Cl2O/c8-6-2-1-5(4-10)7(9)3-6/h1-4H

to

InChI=1S/C11H7Cl3N4/c12-8-2-1-7(9(13)3-8)4-16-18-11-6-15-5-10(14)17-11/h1-6H,(H,17,18)/b16-4+

ClC1=CN=CC(NN)=N1

and

[H]C(C1=CC=C(Cl)C=C1Cl)=O

to

ClC1=CN=CC(N/N=C/C2=CC=C(Cl)C=C2Cl)=N1

3rd April 2017 @ 12:53

At the start of the series four campaign, OSM inherited data for MMV669844, an enantioenriched compound. No ee data was obtained however.

David Edwards and Mark Butler from The University of Queensland performed a chiral resolution and the full report is attached here: 

Purification of AEW313-1 Report 20March17.docx


Attached Files