All Notebooks | Help | Support | About
4th August 2015 @ 03:03

 

SGS 6-2 (118 mg, 0.51 mmol, 1 eq) was added to toluene (~3.5 mL) along with AEW 221-2 (114 mg, 0.51 mmol, 1 eq), potassium hydroxide (100 mg, 1.18 mmol, 3.5 eq) and 18-crown-6 (9.5 mg, 0.036 mmol, 0.07 eq). The mixture was stirred (10 min, 25oC) then heated (40oC).

Water (~4 mL) was added to the product and extracted with ethyl acetate (3×10 mL). The combined organic layers were combined and washed with water (4 mL) until aqeuous layer was neutral. The organic layer was washed with brine (~3 mL) and dried over Na2SO4. The solvent was remved to leave the product.

Hazard and Risk Assessment:

hazard-and-assessment-form.doc

Strings:

ClC1=CN=CC2=NN=C(C3=NC=CC=C3)N12

and

OCC(OC1OCCCC1)C2=CC=CC=C2

to

C1(OCC(OC2OCCCC2)C3=CC=CC=C3)=CN=CC4=NN=C(C5=NC=CC=C5)N14

 

InChI=1S/C10H6ClN5/c11-8-5-12-6-9-14-15-10(16(8)9)7-3-1-2-4-13-7/h1-6H

and

InChI=1S/C13H18O3/c14-10-12(11-6-2-1-3-7-11)16-13-8-4-5-9-15-13/h1-3,6-7,12-14H,4-5,8-10H2

to

InChI=1S/C23H23N5O3/c1-2-8-17(9-3-1)19(31-22-11-5-7-13-29-22)16-30-21-15-24-14-20-26-27-23(28(20)21)18-10-4-6-12-25-18/h1-4,6,8-10,12,14-15,19,22H,5,7,11,13,16H2

Linked Entries
Attached Files
12th July 2015 @ 16:12

SGS 7-1 and 7-2 were washed in with ethyl acetate and solvents were removed. Both samples were analysed with 1H NMR (300 MHz, CDCl3). The 7-1 sample was purified by column chromatography using ethyl acetate and petroleum eluent as some impurities were detected by TLC. The resulting fractions were combined to form 5 fractions.

Based on previous NMR results of this particular compound (AEW 94, DS 3, DS 8) it is likely that the product is present in fraction 1 and 2 only.

Data:

SGS 7-1 CDCl3

SGS 7-1 CDCl3 300 MHz AEW and PK.pdf
SGS 7-1 CDCl3 AEW and PK.zip

SGS 7-2 CDCl3

SGS 7-2 CDCl3 300 MHz AEW and PK.pdf
SGS 7-2 CDCl3 AEW and PK.zip

Column Fractions:

SGS 7-1 frac 1.pdf
SGS 7-1 frac 2.pdf
SGS 7-1 frac 3.pdf
SGS 7-1 frac 4.pdf
SGS 7-1 frac 5.pdf

Strings:

SMILES: ClC1=CN=CC2=NN=C(C3=CC=C(C#N)C=C3)N21

InChi: InChI=1S/C12H6ClN5/c13-10-6-15-7-11-16-17-12(18(10)11)9-3-1-8(5-14)2-4-9/h1-4,6-7H

Attached Files
12th July 2015 @ 15:54

The product provided contained solvent which was washed and then removed with ethyl acetate (~100 mL). However, this brown product also contained a greasy contaminant that did not evaporate under vacuum (20 mPa, 40oC, ~6 h). Nevertheless, the product was analysed with 1H NMR (200 MHz, DMSO). As the product was found to have impurities, it was purified by column chromatography with ethyl acetate and hexane. The columned product was analysed with NMR (200 MHz, CDCl3).

Data:

Pre-column:

SGS 9-1 DMSO AEW and PK.pdf
SGS 9-1 DMSO AEW and PK.zip

Post-column:

SGS 9-1 column.pdf
SGS 9-1 column.zip

Strings:

SMILES: ClC1=CN=CC2=NN=C(C3=CC=NC=C3)N21

InChI=1S/C10H6ClN5/c11-8-5-13-6-9-14-15-10(16(8)9)7-1-3-12-4-2-7/h1-6H

Attached Files
12th July 2015 @ 15:29

The solvents were removed by washing with ethyl acetate (~100 mL), and the SGS 8-1 left under high vacuum. The remaining dark brown solid was contaminated with an unknown, greasy compound and could not be completely dried in 20 mPa, 40oC or under high vacuum, 25oC.

Nevertheless, the sample was analysed by 1H NMR (300 MHz) in CDCl3.

The product was purified with column chromatography in ethyl acetate and hexane then analysed with NMR (200 MHz, CDCl3).

Note: Files are shown as 8-2 but are in fact, 8-1 due to an error in labelling.

Data:

SGS 8-1 CDCl3 300 MHz AEW and PK.pdf
SGS 8-1 CDCl3 AEW and PK.zip

SGS 8-2 Paul Columned.pdf
SGS 8-2 Paul Columned.zip

Strings:

SMILES: ClC1=CN=CC2=NN=C(C3=CC=CN=C3)N21

InChI=1S/C10H6ClN5/c11-8-5-13-6-9-14-15-10(16(8)9)7-2-1-3-12-4-7/h1-6H

Attached Files
12th July 2015 @ 13:59

SGS 6-2 was fully dissolved by adding ethyl acetate (~300 mL), dichloromethane (~10 mL), methanol (~10 mL), and washed with water (~30 mL) then brine (~70 mL). The organic layer was collected and dried with sodium sulfate and the solvent was removed. 

The crude product was dissolved in dichloromethane (~100 mL), ethyl acetate (~50 mL), and methanol (~1 mL). Silica was added and the solvent was removed under vacuum and the SGS 6-2 product was separated by column chromatography. Fractions were combined based on TLC character into 8 larger fractions. Based on NMR data, it was concluded that the most likely fraction containing the desired product was fraction 3.

Data:

SGS 6-2 Frac One.pdf
SGS 6-2 Frac Two.pdf
SGS 6-2 Frac 3.pdf
SGS 6-2 Frac 5.pdf
SGS 6-2 Frac 6.pdf
SGS 6-2 Frac 7.pdf
SGS 6-2 Frac 8.pdf
SGS 6-2 Frac 1-8.zip

Strings:

SMILES: ClC1=CN=CC2=NN=C(C3=NC=CC=C3)N21

InChI=1S/C10H6ClN5/c11-8-5-12-6-9-14-15-10(16(8)9)7-3-1-2-4-13-7/h1-6H

Attached Files