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29th August 2014 @ 03:14

55-1 scheme

 

TM 52 (pure, 170 mg, 0.393 mmol: Synthesis of (E)-N-(3-chlorophenyl)-6-(2-(4-(trifluoromethoxy)benzylidene)hydrazinyl)pyrazine-2-carboxamide (TM 52-1)) was stirred into DCM (6 mL), PIDA (130 mg, 0.393 mmol, 1 eq) added, and the reaction mixture stirred at rt for ?? h.

 

InChIs:

InChI=1S/C19H13ClF3N5O2/c20-13-2-1-3-14(8-13)26-18(29)16-10-24-11-17(27-16)28-25-9-12-4-6-15(7-5-12)30-19(21,22)23/h1-11H,(H,26,29)(H,27,28)/b25-9+

to

InChI=1S/C19H11ClF3N5O2/c20-12-2-1-3-13(8-12)25-18(29)15-9-24-10-16-26-27-17(28(15)16)11-4-6-14(7-5-11)30-19(21,22)23/h1-10H,(H,25,29)

HIRAC:

HIRAC.pdf

Attached Files
29th August 2014 @ 01:36

54 scheme

 

TM 51 (pure, 150 mg, 0.393 mmol: Synthesis of (E)-N-(3-chlorophenyl)-6-(2-(4-methoxybenzylidene)hydrazinyl)pyrazine-2-carboxamide (TM 51-1)) was stirred into DCM (6 mL), PIDA (130 mg, 0.393 mmol, 1 eq) added, and the reaction mixture stirred at rt for ?? g.

InChIs:

InChI=1S/C19H16ClN5O2/c1-27-16-7-5-13(6-8-16)10-22-25-18-12-21-11-17(24-18)19(26)23-15-4-2-3-14(20)9-15/h2-12H,1H3,(H,23,26)(H,24,25)/b22-10+

to

InChI=1S/C19H14ClN5O2/c1-27-15-7-5-12(6-8-15)18-24-23-17-11-21-10-16(25(17)18)19(26)22-14-4-2-3-13(20)9-14/h2-11H,1H3,(H,22,26)

 

HIRAC:

54 HIRAC.pdf

Attached Files
27th August 2014 @ 01:51

Attempt to change order of steps for triazolopyrazine core synthesis so that electron rich amides can be incorporated.

 

6-Chloropyrazine-2-carboxylic acid (100 mg, 0.63 mmol, 1.00 equiv.) and NH3 (0.06 mL, 1.26 mmol, 2.00 equiv.) were dissolved in deuterated DMSO (1 mL). Potassium carbonate (87 mg, 0.26 mmol, 1.35 equiv.) was added and the reaction mixture was heated to 120 ˚C (started: 12 pm).

 

Data:

 

Hazard and Risk Assessment:

HIRAC AEW 196-1.pdf
 

InChi:

InChI=1S/C5H3ClN2O2/c6-4-2-7-1-3(8-4)5(9)10/h1-2H,(H,9,10)

to

InChI=1S/C5H6N4O2/c6-9-4-2-7-1-3(8-4)5(10)11/h1-2H,6H2,(H,8,9)(H,10,11)

 

Smiles:

ClC1=CN=CC(C(O)=O)=N1

to

O=C(O)C1=NC(NN)=CN=C1

 

Literature Reference:

StructureActivity Studies of Diazabicyclo[3.3.0]octane-Substituted Pyrazines and Pyridines as Potent α4β2 Nicotinic Acetylcholine Receptor Ligands 

M. J. C. Scanio, L Shi, W. H. Bunnelle, D. J. Anderson, R. J. Helfrich, J Malysz, K K. Thorin-Hagene, C. E. Van Handel, K. C. Marsh, C-H. Lee, M Gopalakrishnan.

dx.doi.org/10.1021/jm201045m |J. Med. Chem. 2011, 54, 7678–7692 


Attached Files
27th August 2014 @ 01:23

 

AEW 97-12 (50 mg, 0.20 mmol, 1.00 equiv.) and NH3 (0.06 mL, 0.98 mmol, 5.00 equiv. 28% aq. soln) were dissolved in deuterated DMSO (0.5 mL). Potassium carbonate (36 mg, 0.26 mmol, 1.35 equiv.) was added and the reaction mixture was heated to 120 ˚C (started: 12 pm).

 

Data:

 

Hazard and Risk Assessment:

HIRAC AEW 195-1.pdf

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

to

InChI=1S/C12H8N6/c13-5-8-1-3-9(4-2-8)12-17-16-11-7-15-6-10(14)18(11)12/h1-4,6-7H,14H2

Smiles:

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

to

NC1=CN=CC2=NN=C(C3=CC=C(C#N)C=C3)N21


Literature Reference:

StructureActivity Studies of Diazabicyclo[3.3.0]octane-Substituted Pyrazines and Pyridines as Potentα4β2 Nicotinic Acetylcholine Receptor Ligands 

M. J. C. Scanio, L Shi, W. H. Bunnelle, D. J. Anderson, R. J. Helfrich, J Malysz, K K. Thorin-Hagene, C. E. Van Handel, K. C. Marsh, C-H. Lee, M Gopalakrishnan.

dx.doi.org/10.1021/jm201045m |J. Med. Chem. 2011, 54, 7678–7692


Attached Files
23rd August 2014 @ 09:41

 

Procedure:

AEW 175-2 (500 mg, 4.80 mmol, 1 equiv.) was dissolved in DMF (6 mL) under Ar. Cs2CO3 (1.56 g, 4.80 mmol, 1 equiv.) was added and the reaction mixture was stirred at room temperature for 10 minutes. MeI (0.32 mL, 5.28mmol, 1.1 equiv.) was then added and the reaction stirred at room temperature for 2.5 days. 1:1 product: SM

The reaction mixture was diluted with EtOAc (12 mL) and washed with water (5 x 8 mL). Combined aqueous layers were washed withe EtOAc (10 mL) and then combined organic layers were washed with brine (6 mL), dried (MgSO4), filtered and evaporated to give a yellow oil - still DMF in crude proton.

Data:

AEW 194-1 crude proton.pdf
AEW 194-1 crude proton.mnova

Hazard and Risk Assessment:


InChi:

InChI=1S/C3H6O3/c1-2(4)3(5)6/h2,4H,1H3,(H,5,6)

to

InChI=1S/C5H10O3/c1-4(7-2)5(6)8-3/h4H,1-3H3


Smiles:

OC(C)C(O)=O

to

O=C(OC)C(C)OC

Attached Files