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28th April 2015 @ 05:29

Scale up:

needs IR, C13, F19, HRMS and m.p. HIRAC

Crude AEW 225-2 (10.4 mmol) was dissolved in CH2Cl2 (100 mL) (orange/brown solution) and PIDA (3.35 g, 1.04 mmol, 1 equiv.) was added and the reaction mixture stirred at room temperature for 15 hours. (Brown ppt turned to orange red solution).

The reaction was stopped and the organic layer washed with saturated NaHCO3 solution (30 mL x 2). The inorganic layer was extracted with CH2Cl2 (3 x 30 mL). The combined organic layers were washed with saturated NaHCO3 solution (30 mL), brine (30 mL), dried (MgSO4), filtered and evaporated to yield a pale brown solid that was purified by flash column chromatography using the Biotage Isolera: 100 g column, sample dissolved in toluene and loaded as a solution (15-100% EtOAc in petroleum benzine).

The product was obtained as a yellow powder (2.65 g, 8.79 mmol, 96% yield) over two steps.

Data:

TLC (50/50 EtOAc/Hex)

AEW 227-1 (50:50 EtOAc Hexane).JPG
50:50 EtOAc:Hexane 226:227:224.JPG

200 MHz NMR: Product

AEW 227-1 col.pdf
AEW 227.zip

Hazard and Risk Assessment:


Strings:

InChI=1S/C11H7ClF3N5/c12-9-5-16-6-10(19-9)20-18-4-7-1-2-8(17-3-7)11(13,14)15/h1-6H,(H,19,20)/b18-4+

to

InChI=1S/C11H5ClF3N5/c12-8-4-16-5-9-18-19-10(20(8)9)6-1-2-7(17-3-6)11(13,14)15/h1-5H

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

to

ClC1=CN=CC2=NN=C(C3=CN=C(C(F)(F)F)C=C3)N21

Linked Entries
Attached Files
28th April 2015 @ 05:28

GitHub Issue:

needs IR, C13, HRMS and m.p. HIRAC 

Crude AEW 224-2 (~10.4 mmol) was dissolved in CH2Cl2 (100.4 mL) (orange/brown solution) and PIDA (3.35 g, 10.4 mmol, 1 equiv.) was added and the reaction mixture stirred at room temperature for 7 hours. TLC complete.

The reaction was stopped and the organic layer washed with saturated NaHCO3 solution (30 mL x 2). The inorganic layer was extracted with CH2Cl2 (3 x 30 mL). The combined organic layers were washed with saturated NaHCO3 solution (30 mL), brine (30 mL), dried (MgSO4), filtered and evaporated to yield a pale brown solid that was purified by flash column chromatography using the Biotage Isolera: 100 g column, sample dissolved in toluene and loaded as a solution (15-100% EtOAc in petroleum benzine).

aew 226-2_frac.pdf

The product was obtained as an orange solid (2.02 g, 8.54 mmol, 82% yield) over two steps.

Data:

TLC (50/50 EtOAc/Hex)

Data:

TLC (50/50 EtOAc/Hexane)

50:50 EtOAc:Hexane 226:227:224.JPG
AEW 226-2 (EtOAc:Hex 50:50).JPG
 

200 MHz NMR: Product

AEW 226-2 col.zip
TOPSPIN Plot Layout.pdf

Hazard and Risk Assessement:

see:

HIRAC AEW 218-1.pdf
 

Strings:

InChI=1S/C11H15ClN4/c12-10-7-13-8-11(15-10)16-14-6-9-4-2-1-3-5-9/h6-9H,1-5H2,(H,15,16)/b14-6+

to

InChI=1S/C11H13ClN4/c12-9-6-13-7-10-14-15-11(16(9)10)8-4-2-1-3-5-8/h6-8H,1-5H2

 

ClC1=CN=CC(N/N=C/C2CCCCC2)=N1

to

ClC1=CN=CC2=NN=C(C3CCCCC3)N21

Attached Files
21st April 2015 @ 05:49

GitHub Isuue #275

needs IR, C13, HRMS and m.p. HIRAC 

Crude AEW 222-1 (~10.4 mmol) was dissolved in CH2Cl2 (100.4 mL) (orange/brown solution) and PIDA (3.35 g, 10.4 mmol, 1 equiv.) was added and the reaction mixture stirred at room temperature for 15 hours.

The reaction was stopped and the organic layer washed with saturated NaHCO3 solution (30 mL x 2). The inorganic layer was extracted with CH2Cl2 (3 x 30 mL). The combined organic layers were washed with saturated NaHCO3 solution (30 mL), brine (30 mL), dried (MgSO4), filtered and evaporated to yield a pale brown solid that was purified by flash column chromatography using the Biotage Isolera: 100 g column, sample dissolved in toluene and loaded as a solution (15-100% EtOAc in petroleum benzine).

The product was obtained in two fractions and then combined following NMR analysis: 

Yellow solid (2.09 g, 9.08 mmol, 87% yield).

Data:

TLC (50/50 EtOAc/Hex)

AEW 223-3 (50:50 EtOAc:Hex).png

Column

aew 223-1_frac.pdf

200 MHz columned product: Looks good.

9.89 (1H, s), 7.87 (1H, s), 7.56-7.47 (5H, m).

First fracs

AEW 223-1 columned.pdf
AEW 223-1 column.zip

Second fracs

AEW 223-1 col last frac.pdf
AEW 223-1 column last frac.zip

Both combined.

Hazard and Risk Assessement:

see:

HIRAC AEW 218-1.pdf
 

Strings:

InChI=1S/C11H9ClN4/c12-10-7-13-8-11(15-10)16-14-6-9-4-2-1-3-5-9/h1-8H,(H,15,16)/b14-6+

to

InChI=1S/C11H7ClN4/c12-9-6-13-7-10-14-15-11(16(9)10)8-4-2-1-3-5-8/h1-7H

 

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

to

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

Attached Files
21st April 2015 @ 05:48

needs IR, C13, HRMS and m.p. HIRAC 

GitHub Isuue #275


Crude AEW 217-1 (~10.4 mmol) was dissolved in CH2Cl2 (100.4 mL) (orange/brown solution) and PIDA (3.35 g, 10.4 mmol, 1 equiv.) was added and the reaction mixture stirred at room temperature for 16 hours.

The reaction was stopped and the organic layer washed with saturated NaHCO3 solution (30 mL x 2). The inorganic layer was extracted with CH2Cl2 (3 x 30 mL). The combined organic layers were washed with saturated NaHCO3 solution (30 mL), brine (30 mL), dried (MgSO4), filtered and evaporated to yield a pale brown solid that was purified by flash column chromatography using the Biotage Isolera: 100 g column, sample dissolved in toluene and loaded as a solution (15-100% EtOAc in petroleum benzine).

The product was obtained in two fractions.

Fraction Two orange solid (975 mg, 5.34 mmol, 51% yield) over two steps.

Fraction One

 

Data:

TLC (50/50 EtOAc/Hex): 

AEW 218-2 (50:50 EtOAc:Hexane).png

Column:

aew 218-2_frac.pdf

200 MHz NMR: Product

AEW 218-2 col.pdf
AEW 218-2 col.zip

Hazard and Risk Assessement:

HIRAC AEW 218-1.pdf
 

Strings:

InChI=1S/C7H9ClN4/c1-2-3-10-12-7-5-9-4-6(8)11-7/h3-5H,2H2,1H3,(H,11,12)/b10-3+

to

InChI=1S/C7H7ClN4/c1-2-6-10-11-7-4-9-3-5(8)12(6)7/h3-4H,2H2,1H3

 

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

to

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

Attached Files
1st December 2013 @ 22:31

Missing NMR data file..find and ask Ian

Zinc Chloride was purified by refluxing in thionyl chloride (thanks Kat Badiola!)

 

ZnCl2 (96 mg, 0.7 mmol) was weighed into an oven-dried flask under Ar. 3,4-Difluorobenzaldehyde (100 mg, 0.7 mmol) was dissolved in CH2Cl2 (0.6 mL) and added at 0 ˚C  and then TMSCN (70 mg, 0.09 mL, 0.7 mmol) was added at 0 ˚C and the reaction mixture stirred at 0 ˚C for 30 minutes. Still SM. Stirred for a further 30 minutes and then for 2.5 h whilst reaching room temperature. The reaction mixture was poured into water (5 mL) and then extracted with EtOAc (2 x 10 mL), dried over MgSO4, filtered and evaporated (TOXIC BUCHI) to give a pale brown oil (1.38 g) that was used without further purification.

Data:

Missing NMR file but good conversion to product and some of the product without TMS group

Hazard and Risk Assessment:

HIRAC AEW 94-6.pdf

 InChi:

InChI=1S/C7H4F2O/c8-6-2-1-5(4-10)3-7(6)9/h1-4H

goes to

InChI=1S/C11H13F2NOSi/c1-16(2,3)15-11(7-14)8-4-5-9(12)10(13)6-8/h4-6,11H,1-3H3