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1st September 2014 @ 00:05

Repeat synthesis of JU 1-20 to validate new conditions. 

Reaction Scheme

Procedure

Started 9:50am

2,6-Dichloropyrazine (Aldrich, 1.00 g, 6.8 mmol) was dissolved in ethanol (10 mL) to give a clear solution. Hydrazine hydrate (1.0 mL, 1.0 g, 20.4 mmol, 3 equiv) was added resulting in a pale yellow solution. The resulting mixture was heated at reflux (bath temperature 100˚C) for 4 h. Analysis by TLC showed the reaction was complete.

TLC JU 1-21:22 30:70 EtOAc:Hex 4 h.jpg
 

The reaction was cooled to room temp then further in an ice bath for 1 h (due to meeting) before the solvent was removed by rotary evaporation and dried in vacuo. The crude product (1.68 g, 170% crude yield) was pale yellow fluffy needles and was analysed by 1H NMR and found to be the correct product.

1H NMR, crude, DMSO, 300 MHz

JU 1-22 crude 300 MHz.pdf
JU 1-22 crude.zip

 

HIRAC & Risk Assessment

See JU 1-1

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)

SMILES

ClC1=CN=CC(Cl)=N1

to

ClC1=CN=CC(NN)=N1

Attached Files
31st August 2014 @ 23:59

Repeat synthesis of JU 1-20 to validate new conditions. 

Reaction Scheme

Procedure

Started 9:50am

2,6-Dichloropyrazine (Aldrich, 1.00 g, 6.8 mmol) was dissolved in ethanol (10 mL) to give a clear solution. Hydrazine hydrate (1.0 mL, 1.0 g, 20.4 mmol, 3 equiv) was added resulting in a pale yellow solution. The resulting mixture was heated at reflux (bath temperature 100˚C) for 4 h. Analysis by TLC showed the reaction was complete.

TLC JU 1-21:22 30:70 EtOAc:Hex 4 h.jpg

The reaction was cooled to room temp then further in an ice bath for 1 h (due to meeting) before the solvent was removed by rotary evaporation and dried in vacuo. The crude product (1.48 g, 150% crude yield) was pale yellow fluffy needles and was analysed by 1H NMR and found to be the correct product.  

1H NMR, crude, DMSO, 300 MHz

JU 21-1 crude 300 MHz.pdf
JU 1-21 crude.zip

 

HIRAC & Risk Assessment

See JU 1-1

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)

SMILES

ClC1=CN=CC(Cl)=N1

to

ClC1=CN=CC(NN)=N1

Attached Files
30th August 2014 @ 04:01

 Started Friday afternoon (4:30 pm) posted Saturday.

 

Procedure:

AEW 189-1 *purified (500 mg, 4.23 mmol, 1 equiv.) was dissolved in DMF (6 mL) under Ar. Cs2CO3 (1.38 g, 4.23 mmol, 1 equiv.) was added and the reaction mixture was stirred at room temperature for 10 minutes. MeI (0.29 mL, 4.66 mmol, 1.1 equiv.) was then added and the reaction stirred at room temperature overnight (11 am Sat). TLC indicated spot to spot conversion with poduct much lower Rf (unexpected) >0.1 50:50 EtOAc/Hex.

The reaction mixture was diluted with EtOAc (12 mL) and washed with water (5 x 8 mL). Combined aqueous layers were washed with EtOAc (10 mL) and then combined organic layers were washed with brine (6 mL), dried (MgSO4), filtered and evaporated to give

Data:

 

Hazard and Risk Assessment:

See Synthesis of methyl 2-methoxy-2-methylpropanoate (AEW 193-1)

InChi:

InChI=1S/C4H8O3/c1-4(2,7)3(5)6/h7H,1-2H3,(H,5,6)

to

InChI=1S/C6H12O3/c1-6(2,9-4)5(7)8-3/h1-4H3


Smiles:

OC(C)(C)C(O)=O

to

O=C(OC)C(C)(C)OC

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
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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
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