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12th December 2013 @ 05:12

Postponed until tomorrow as microwave not accessible today

 

A solution of AEW 98-1 (29 mg, 0.12 mmol, 1 equiv.), MNR 103-  (40 mg,  0.14 mmol, 1.2 equiv.) and PdCl2dppf (17 mg, 0.02 mmol, 0.20 equiv.) in isopropanol (2.4 mL) and K2CO3 (1 M, 0.24 mL, 0.22 mmol, 2.0 equiv.) was degassed with argon for 10 minutes.

The reaction mixture was heated at 90 oC for 30 minutes in a microwave reactor (200 W).

Hazard and Risk Assessment:

See http://malaria.ourexperiment.org/uri/3da and links within

 

InChi:

InChI=1S/C7H6BrN3S/c1-9-7-6-4(10-3-11-7)2-5(8)12-6/h2-3H,1H3,(H,9,10,11)

and

InChI=1S/C12H18BNO4S/c1-11(2)12(3,4)18-13(17-11)9-6-5-7-10(8-9)19(14,15)16/h5-8H,1-4H3,(H2,14,15,16)

to

InChI=1S/C13H12N4O2S2/c1-15-13-12-10(16-7-17-13)6-11(20-12)8-3-2-4-9(5-8)21(14,18)19/h2-7H,1H3,(H2,14,18,19)(H,15,16,17)

Attached Files
12th December 2013 @ 04:53

 

A solution of AEW 100 (25 mg, 0.11 mmol, 1 equiv.), AEW 90 (40 mg,  0.13 mmol, 1.2 equiv.) and PdCl2dppf (16 mg, 0.02 mmol, 0.20 equiv.) in isopropanol (2.1 mL) and K2CO3 (1 M, 0.21 mL, 0.21 mmol, 2.0 equiv.) was degassed with argon for 10 minutes.

The reaction mixture was heated at 90oC for 30 minutes in a microwave reactor (200 W).

Hazard and Risk Assessment:

See http://malaria.ourexperiment.org/uri/3da and links within

 

InChi:

InChI=1S/C6H4BrN3S/c7-4-1-3-5(11-4)6(8)10-2-9-3/h1-2H,(H2,8,9,10)

and

InChI=1S/C14H22BNO4S/c1-13(2)14(3,4)20-15(19-13)11-8-7-9-12(10-11)21(17,18)16(5)6/h7-10H,1-6H3

to

InChI=1S/C14H14N4O2S2/c1-18(2)22(19,20)10-5-3-4-9(6-10)12-7-11-13(21-12)14(15)17-8-16-11/h3-8H,1-2H3,(H2,15,16,17)

Attached Files
12th December 2013 @ 02:31

 

A solution of AEW 100 (26 mg, 0.11 mmol, 1 equiv.), AEW 69-1 (40 mg,  0.13 mmol, 1.2 equiv.) and PdCl2dppf (16 mg, 0.02 mmol, 0.20 equiv.) in isopropanol (2.2 mL) and K2CO3 (1 M, 0.24 mL, 0.22 mmol, 2.0 equiv.) was degassed with argon for 10 minutes.

The reaction mixture was heated at 90oC for 30 minutes in a microwave reactor (200 W).

Hazard and Risk Assessment:

See http://malaria.ourexperiment.org/uri/3da and links within

 

InChi:

InChI=1S/C6H4BrN3S/c7-4-1-3-5(11-4)6(8)10-2-9-3/h1-2H,(H2,8,9,10)

and

InChI=1S/C13H20BNO4S/c1-12(2)13(3,4)19-14(18-12)10-7-6-8-11(9-10)20(16,17)15-5/h6-9,15H,1-5H3

to

InChI=1S/C13H12N4O2S2/c1-15-21(18,19)9-4-2-3-8(5-9)11-6-10-12(20-11)13(14)17-7-16-10/h2-7,15H,1H3,(H2,14,16,17)

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Attached Files
12th December 2013 @ 01:23

 

A solution of AEW 100 (23 mg, 0.1 mmol, 1 equiv.), AEW 92-1 (40 mg,  0.12 mmol, 1.2 equiv.) and PdCl2dppf (14 mg, 0.02 mmol, 0.20 equiv.) in isopropanol (2.0 mL) and K2CO3 (1 M, 0.20 mL, 0.20 mmol, 2.0 equiv.) was degassed with argon for 10 minutes.

The reaction mixture was heated at 90 oC for 30 minutes in a microwave reactor (200 W). Reaction mixture turned from red mixture to black. The RM was diluted with MeOH (10 mL), filtered over CeliteTM, washed with MeOH (4 x 10 mL), filtered and evaporated to give a black solid.

Purification by flash column chromatography over silica:

Data:

TLC (95:4.5:0.5 CH2Cl2/MeOH/NH4)

AEW 105-1 1st.jpg
AEW 105-1 2nd.jpg

First and second elution of same plate - shows SM and product have similar Rf but reaction complete.

Hazard and Risk Assessment:

See http://malaria.ourexperiment.org/uri/3da and links within

 

InChi:

InChI=1S/C6H4BrN3S/c7-4-1-3-5(11-4)6(8)10-2-9-3/h1-2H,(H2,8,9,10)

and

InChI=1S/C16H24BNO4S/c1-15(2)16(3,4)22-17(21-15)13-8-7-9-14(12-13)23(19,20)18-10-5-6-11-18/h7-9,12H,5-6,10-11H2,1-4H3

to

InChI=1S/C16H16N4O2S2/c17-16-15-13(18-10-19-16)9-14(23-15)11-4-3-5-12(8-11)24(21,22)20-6-1-2-7-20/h3-5,8-10H,1-2,6-7H2,(H2,17,18,19)

Attached Files