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17th April 2014 @ 00:40

Literature reference: 10.1021/jo901707x

GitHub link:

Reaction Scheme

Procedure

Started

2-­‐(3-­‐Chlorophenyl)ethylamine (x mL, x mg, x mmol, x equiv) was added to 1 mL toluene along with JU 3-7 (x mg, x mmol, x equiv), potassium hydroxide (x mg, x mmol, x equiv) and 18-crown-6 (x mg, x mmol, x equiv). The reaction was stirred for x h.

 

HIRAC

HIRAC JU 11-1.pdf

InChI strings

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

and

InChI=1S/C8H10ClN/c9-8-3-1-2-7(6-8)4-5-10/h1-3,6H,4-5,10H2

to

InChI=1S/C20H15ClN6/c21-17-3-1-2-14(10-17)8-9-24-18-12-23-13-19-25-26-20(27(18)19)16-6-4-15(11-22)5-7-16/h1-7,10,12-13,24H,8-9H2

SMILES

N#CC(C=C1)=CC=C1C2=NN=C3C=NC=C(Cl)N32

and

NCCC1=CC(Cl)=CC=C1

to

N#CC(C=C1)=CC=C1C2=NN=C3C=NC=C(NCCC4=CC(Cl)=CC=C4)N32

Attached Files
16th April 2014 @ 04:15

Synthesis of series 4 amide.

scheme

 

Purified TM 12-1 (see Synthesis of (E)-N-(3-chlorophenyl)-6-(2-(4-(difluoromethoxy)benzylidene)hydrazinyl)pyrazine-2-carboxamide (TM 12-1)) (70 mg, 0.17 mmol) was combined with chloramine-T (1.2 eq, 0.20 mmol, 57 mg) in 2-MeTHF (1.5 mL), and heated at 60 oC for ?? hours.

 

 

InChIs:

InChI=1S/C19H14ClF2N5O2/c20-13-2-1-3-14(8-13)25-18(28)16-10-23-11-17(26-16)27-24-9-12-4-6-15(7-5-12)29-19(21)22/h1-11,19H,(H,25,28)(H,26,27)/b24-9+

to

InChI=1S/C19H12ClF2N5O2/c20-12-2-1-3-13(8-12)24-18(28)15-9-23-10-16-25-26-17(27(15)16)11-4-6-14(7-5-11)29-19(21)22/h1-10,19H,(H,24,28)

 

HIRAC:

HIRAC.pdf

Attached Files
16th April 2014 @ 00:23

Literature reference: 10.1021/jo901707x

GitHub link: #183

Reaction Scheme

Procedure

Started

2-chlorophenethyl alcohol (x mL, x mg, x mmol, x equiv) was added to 1 mL toluene along with JU 3-7 (x mg, x mmol, x equiv), potassium hydroxide (x mg, x mmol, x equiv) and 18-crown-6 (x mg, x mmol, x equiv). The reaction was stirred for x h.

 

HIRAC

HIRAC JU 10-1.pdf

InChI strings


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


and

InChI=1S/C8H9ClO/c9-8-4-2-1-3-7(8)5-6-10/h1-4,10H,5-6H2

to

InChI=1S/C20H14ClN5O/c21-17-4-2-1-3-15(17)9-10-27-19-13-23-12-18-24-25-20(26(18)19)16-7-5-14(11-22)6-8-16/h1-8,12-13H,9-10H2

SMILES

N#CC(C=C1)=CC=C1C2=NN=C3C=NC=C(Cl)N32

and

OCCC1=CC=CC=C1Cl

to

N#CC(C=C1)=CC=C1C2=NN=C3C=NC=C(OCCC4=CC=CC=C4Cl)N32

Attached Files
15th April 2014 @ 14:22

 

Procedure:

Crude AEW 134-1 (~0.71 mmol, 1 equiv.) was combined with Chloramine-T (239 mg, 0.85 mmol, 1.2 equiv.) in 2-methyltetrahydrofuran 53.7 mL) and the reaction mixture was heated to 60 ˚C for 1.5 hours.

Reaction mixture turned from yellow ppt to brown solution.

After 2 h , the reaction mixture was removed from the oil bath, diluted with 2-MeTHF (12 mL) and washed with 10 wt% aq. sodium sulfite solution (6 mL), 1 M sodium hydroxide solution (2 x 6 mL) and then evaporated to dryness to give a dark brown oil.

Crude NMR

 

InChi:

InChI=1S/C20H14ClF4N5O2/c21-16-6-3-14(22)7-13(16)9-27-19(31)17-10-26-11-18(29-17)30-28-8-12-1-4-15(5-2-12)32-20(23,24)25/h1-8,10-11H,9H2,(H,27,31)(H,29,30)/b28-8-

to

InChI=1S/C20H12ClF4N5O2/c21-15-6-3-13(22)7-12(15)8-27-19(31)16-9-26-10-17-28-29-18(30(16)17)11-1-4-14(5-2-11)32-20(23,24)25/h1-7,9-10H,8H2,(H,27,31)

 

Attached Files
15th April 2014 @ 14:17

 

Procedure:

Crude AEW 134-1 (~0.71 mmol, 1 equiv.) was combined with Chloramine-T (239 mg, 0.85 mmol, 1.2 equiv.) in 2-methyltetrahydrofuran 53.7 mL) and the reaction mixture was heated to 60 ˚C for 1.5 hours.

Reaction mixture turned from yellow ppt to brown solution.

After 2 h , the reaction mixture was removed from the oil bath, diluted with 2-MeTHF (12 mL) and washed with 10 wt% aq. sodium sulfite solution (6 mL), 1 M sodium hydroxide solution (2 x 6 mL) and then evaporated to dryness to give a dark brown oil.

Crude NMR

 

InChi:

InChI=1S/C19H14Cl2FN5O/c20-14-3-1-12(2-4-14)8-25-27-18-11-23-10-17(26-18)19(28)24-9-13-7-15(22)5-6-16(13)21/h1-8,10-11H,9H2,(H,24,28)(H,26,27)/b25-8-

to

InChI=1S/C19H12Cl2FN5O/c20-13-3-1-11(2-4-13)18-26-25-17-10-23-9-16(27(17)18)19(28)24-8-12-7-14(22)5-6-15(12)21/h1-7,9-10H,8H2,(H,24,28)

Attached Files