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4th August 2016 @ 02:12

GitHub Issue #400 Resynthesised as part of "Frontrunner" campaign.

(xx mg, 0.xx mmol, xx% yield)

Starting material synthesis: 

 

Procedure:

AEW (500 mg, 1.89 mmol, 1.0 equiv.), potassium hydroxide (370 mg, 6.60 mmol, 3.5 equiv.) and 18-crown-6 (35 mg, 0.13 mmol, 0.07 equiv.) were stirred in toluene (11 mL) and AEW alcohol (419 mg, 1.89 mmol, 1.0 equiv.) was added and the reaction mixture stirred at rt for 30 mins. TLC showed reaction complete (9:1 EtOAc/hex)


Water (20 mL) was added and the mixture was extracted with EtOAc (3 x 40 mL). Combined organic layers were washed with water (20 mL), brine (20 mL), dried (MgSO4) filtered and evaporated to give a pale yellow solid which was purified by flash column chromatography using the Biotage IsoleraTM with handpacked 50 g column and EtOAc gradient. One fraction collected and evaporated to yield the desired product as a pearlescent cream solid (218 mg, 0.051 mmol, 44% yield).

 

Data:

 

Hazard and Risk Assessment:

HIRAC AEW 296-1 .doc

Strings:

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

to

N#CC(C=C1)=CC=C1C2=NN=C3N2C(OCCC4=CC=CC=C4)=CN=C3

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

to

InChI=1S/C20H15N5O/c21-12-16-6-8-17(9-7-16)20-24-23-18-13-22-14-19(25(18)20)26-11-10-15-4-2-1-3-5-15/h1-9,13-14H,10-11H2

Attached Files
AEW 304-1.png
AEW 304-1.cdxml