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1st July 2015 @ 10:28

AEW 85 (340 mg, 2.35 mmol) was stirred into a solution of ethanol (6 mL).

1-Boc-piperidine-3-carboxaldehyde (500 mg, 2.35 mmol) was added and the reaction mixture stirred at room temperature for 

 

Data:

NMR 200 MHz

Hazard and Risk Assessment: 

HIRAC AEW 217-1.pdf

 

Strings:

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

and

InChI=1S/C11H19NO3/c1-11(2,3)15-10(14)12-6-4-5-9(7-12)8-13/h8-9H,4-7H2,1-3H3

to

InChI=1S/C15H22ClN5O2/c1-15(2,3)23-14(22)21-6-4-5-11(10-21)7-18-20-13-9-17-8-12(16)19-13/h7-9,11H,4-6,10H2,1-3H3,(H,19,20)/b18-7+

ClC1=CN=CC(NN)=N1

and

O=C([H])C1CCCN(C1)C(OC(C)(C)C)=O

to

ClC1=CN=CC(N/N=C/C2CCCN(C2)C(OC(C)(C)C)=O)=N1

30th June 2015 @ 06:31

Started at 15:30.

2,6-dichloropyrazine (21 g, 141 mmol) was dissolved in ethanol (282 mL), and hydrazine hydrate (13.5 mL, 270 mmol) was added. The reaction mixture was refluxed (80oC, 7 h).

HIRAC:

hazard-and-assessment-form.pdf

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)

Attached Files
29th June 2015 @ 10:37

Reaction Scheme

Procedure

AEW 204 (~29.1 mmol) was stirred into CH2Cl2 (250 mL). PhI(OAc)(9.37 g, 29.1 mmol) was added and the resulting solution was stirred at room temperature.

 

Reference Spectra:

1H NMR, pure, DMSO, 300 MHz

JU 19-1 pure 300 MHz.pdf

 

 
JU 19-1 pure 13C 300 MHz.pdf

 

 

 

 

 

 

HIRAC

 See 5-chloro-3-(4-(difluoromethoxy)phenyl)-[1,2,4]triazolo[4,3-a]pyrazine (JU 19-1)

InChI strings

InChI=1S/C12H9ClF2N4O/c13-10-6-16-7-11(18-10)19-17-5-8-1-3-9(4-2-8)20-12(14)15/h1-7,12H,(H,18,19)/b17-5+

to

InChI=1S/C12H7ClF2N4O/c13-9-5-16-6-10-17-18-11(19(9)10)7-1-3-8(4-2-7)20-12(14)15/h1-6,12H

SMILES

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

to

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

29th June 2015 @ 08:00

Crude AEW 244-1 (~2.35 mmol) was dissolved in CH2Cl2 (23 mL) (orange/brown solution) and PIDA (757 mg, 2.35 mmol, 1 equiv.) was added and the reaction mixture stirred at room temperature for


Data:



Strings:

ClC1=CN=CC(N/N=C/C2CCCN(C2)C(OC(C)(C)C)=O)=N1

to

ClC1=CN=CC2=NN=C(C3CN(CCC3)C(OC(C)(C)C)=O)N21

InChI=1S/C15H22ClN5O2/c1-15(2,3)23-14(22)21-6-4-5-11(10-21)7-18-20-13-9-17-8-12(16)19-13/h7-9,11H,4-6,10H2,1-3H3,(H,19,20)/b18-7+

to

InChI=1S/C15H20ClN5O2/c1-15(2,3)23-14(22)20-6-4-5-10(9-20)13-19-18-12-8-17-7-11(16)21(12)13/h7-8,10H,4-6,9H2,1-3H3

Attached Files
25th June 2015 @ 04:44

Note replaced solvent (MeCN/AcOH with EtOH to improve procedure)

GitHub Issue 

 

AEW 85 (4.2 g, 29.1 mmol) was stirred into a solution of ethanol (90 mL).

4-(difluoromethoxy)benzaldehyde (5.0 g, 29.1 mmol) was added and the reaction mixture (yellow ppt) was stirred at room temperature for 30 minutes when it solidified (reaction complete), EtOH (20 mL) was added and the rection mixture stirred overnight to yield a yellow ppt. Solvents removed in vacuo to provide a yellow solid (8.72 g, >100%) crude.

NMR shows 5:1 product to aldehyde SM but used directly in next step, will separate aldehyde after cyclisation.

Data:

 

AEW 240 and 244-1.JPG

NMR 200 MHz

AEW 204 crude.pdf
AEW 204 crude.zip

NMR shows 5:1 product to aldehyde SM

Hazard and Risk Assessment: 

HIRAC AEW 217-1.pdf

InChI strings

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

and

InChI=1S/C8H6F2O2/c9-8(10)12-7-3-1-6(5-11)2-4-7/h1-5,8H

to

InChI=1S/C12H9ClF2N4O/c13-10-6-16-7-11(18-10)19-17-5-8-1-3-9(4-2-8)20-12(14)15/h1-7,12H,(H,18,19)/b17-5+


SMILES

ClC1=CN=CC(NN)=N1

and

[H]C(C1=CC=C(OC(F)F)C=C1)=O

to

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


 
Attached Files