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9th December 2014 @ 16:23

Reaction Scheme

Experimental Procedure 

Compound 1 ( 200 mg, 0.66 mmol) was dissolved in EtOH (2.2 mL) and treated with 64% weight hydrazine hydrate in water (0.2 mL, 6.66 mmol , 10 equivs). The reaction was refluxed overnight. 

TLC indicated the reaction was complete as the starting materials had been consumed. The solution was cooled down upon which crystallisation occured. 

The solid was filtered and washed with cold EtOH to yield compound 2 crude ( 100 mg, 50% yield) 

 

SMILES 

ClC1=CC=CC(C(N(C2=CC(C(F)(F)F)=NC=C2)[H])=O)=N1

to 

O=C(N(C1=CC(C(F)(F)F)=NC=C1)[H])C2=NC(NN)=CC=C2

InChI Strings

InChI=1S/C12H7ClF3N3O/c13-10-3-1-2-8(19-10)11(20)18-7-4-5-17-9(6-7)12(14,15)16/h1-6H,(H,17,18,20)

to

InChI=1S/C12H10F3N5O/c13-12(14,15)9-6-7(4-5-17-9)18-11(21)8-2-1-3-10(19-8)20-16/h1-6H,16H2,(H,19,20)(H,17,18,21)

NMR 

JS 14-1.png
Attached Files
9th December 2014 @ 14:10

 

Reaction Scheme 

Procedure

6-Chloropicolinic acid (1000 mg, 6.35 mmol) in thionyl chloride (10ml) was stirred and
heated to reflux for 1 hour. The excess thionyl chloride was evaporated in vacuo .  A solution of 3-chloroaniline (0.67 mL, 6.35 mmol) and triethylamine (0.89 mL, 6.35 mmol) in dichloromethane (10 mL) was added dropwise with stirring, maintaining the temperature below 20° C by submerging the flask in an ice-water bath.  After the addition, the reaction mixture was stirred ovenight at an ambient temperature

Risk Assessment 


JS 1-1.docx

InChI strings

InChI=1S/C6H4ClNO2/c7-5-3-1-2-4(8-5)6(9)10/h1-3H,(H,9,10)

to

InChI=1S/C12H8Cl2N2O/c13-8-3-1-4-9(7-8)15-12(17)10-5-2-6-11(14)16-10/h1-7H,(H,15,17)

SMILES

ClC1=NC(C(O)=O)=CC=C1

to

ClC1=NC(C(NC2=CC=CC(Cl)=C2)=O)=CC=C1

 

8th December 2014 @ 06:15

Reference: http://pubs.acs.org/doi/pdf/10.1021/jo00046a020?source=chemport

 Problems uploading PNG file

To a stirred solution of D-(-)-alpha-phenylglycince (1g, 6.6 mmol) in 8 ml of 8% formic acid at 0 ˚C, was added dropwise acetic anhydride (4.3 mL). The reaction mixture was stirred at room temperature for 10 mins and then warmed to room temperature.

 

1.3 g product

 

 

 

InChI=1S/C8H9NO2/c9-7(8(10)11)6-4-2-1-3-5-6/h1-5,7H,9H2,(H,10,11)

to

InChI=1S/C9H9NO3/c11-6-10-8(9(12)13)7-4-2-1-3-5-7/h1-6,8H,(H,10,11)(H,12,13)

4th December 2014 @ 15:36

Reaction Scheme 

Experimental Procedure

JS 11-1 [Synthesis of 4-(5-chloro-[1,2,4]triazolo[4,3-a]pyridin-3-yl)benzonitrile (JS 11-1)]  (80 mg, 0.315 mmol) was dissolved in toluene (2 mL) and then treated with 2-(2-chlorophenyl)ethanol (0.05 mL, 0.377 mmol). KOH (58 mg, 1 mmol) & 18-crown-6 (9 mg, 0.032 mmol) were then added and the mixture was allowed to stir for 1 hour. 

The mixture was cooled to room temperature before water (6 mL) was added. The phases were separated and the aqueous layer was washed with EtOAc (4 x 5 mL). The organic layer was then washed with water until the aqueous later became neutral. The combined organic layers were dried over Na2SO4 and filtered before removing solvents in vacuo to produce the crude product. An attempt at purifing the product was carried out using dry flash column chromatography however this was unsuccesful.

SMILES 

ClC(C=CC=C1)=C1CCOC2=CC=CC3=NN=C(C4=CC=C(C#N)C=C4)N32

to

ClC(C=CC=C1)=C1CCOC2=CC=CC3=NN=C(C4=CC=C(C#N)C=C4)N32

InChI Strings 

InChI=1S/C21H15ClN4O/c22-18-5-2-1-4-16(18)12-13-27-20-7-3-6-19-24-25-21(26(19)20)17-10-8-15(14-23)9-11-17/h1-11H,12-13H2

to

InChI=1S/C21H15ClN4O/c22-18-5-2-1-4-16(18)12-13-27-20-7-3-6-19-24-25-21(26(19)20)17-10-8-15(14-23)9-11-17/h1-11H,12-13H2

Attached Files
3rd December 2014 @ 12:01

Reaction Scheme

Experimental procedure 


6-chloropicolinic acid (950 mg, 5.24 mmol) was dissolved in thionyl chloride (10 mL) and refluxed for 1 hour. The thionyl chloride was then removed in vacuo to produce the crude acid chloride. This was then used as crude and dissolved in DCM (7 mL) after which it was treated with 2-(trifluoromethyl)pyridin-4-amine (850 mg, 5.24 mmol) and triethylamine (0.73 mL, 5.24 mmol). The reaction stirred overnight at room temperature. 

Water was then added to the solution (15 mL) and the phases were separated. The organic layer was washed with water (4 x 10 mL) and finally with 0.1 M HCl (1 x 10 mL). The combined organic layers were dried over MgSO4 and the solvents were removed in vacuo to yield a crude white solid (1.6 g) .

The crude was purified with dry flash column chromatography. However the desired product still contained minor impurities (yield - 600mg of almost pure product)

SMILES 

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

to

O=C(NC1=CC(C(F)(F)F)=NC=C1)C2=NC(Cl)=CC=C2

InChI Strings 

InChI=1S/C6H4ClNO2/c7-5-3-1-2-4(8-5)6(9)10/h1-3H,(H,9,10)

to

InChI=1S/C12H7ClF3N3O/c13-10-3-1-2-8(19-10)11(20)18-7-4-5-17-9(6-7)12(14,15)16/h1-6H,(H,17,18,20)


NMR 

JS 12-1 .png
Attached Files