N-benzylbut-2-yn-1-amine

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of (Z)-3-methyl-1-(5-methyl-3-(2,2,3,3-tetrafluoro-2,3-dihydrobenzo[b][1,4]dioxin-6-yl)thiazol-2(3H)-ylidenecarbamoyl)-1H-imidazol-3-ium iodide (Example 81A, 0.75 mL of 0.14 M in acetonitrile, 58 mg, 0.1 mmol) was added to a 20 mL vial followed by N,N-diisopropylethylamine (0.75 mL of 0.14 M in acetonitrile, 18 mg, 0.13 mmol). Subsequently, N-benzylbut-2-yn-1-amine (0.57 mL of 0.2 M in acetonitrile, 0.11 mmol) was added. The resulting mixture was shaken at room temperature overnight. It was then concentrated in vacuo and the residue was taken up in 1:1 MeOH/DMSO and purified by reverse phase HPLC (acetonitrile/water 0.1% TFA gradient elution method). 1H NMR (500 MHz, DMSO-d6/D2O) δ ppm 1.75 (3H) 2.24 (3H) 4.05 (2H) 4.55 (2H) 7.01-7.10 (1H) 7.17-7.29 (4H) 7.29-7.35 (1H) 7.40-7.54 (1H) 7.58-7.63 (1H) 7.66-7.94 (1H); MS (ESI+) m/z 506 (M+H)+. It was then concentrated in vacuo purified by reverse phase HPLC (acetonitrile/water 0.1% TFA gradient elution method)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of (Z)-3-methyl-1-(5-methyl-3-(2,2,3,3-tetrafluoro-2,3-dihydrobenzo[b][1,4]dioxin-6-yl)thiazol-2(3H)-ylidenecarbamoyl)-1H-imidazol-3-ium iodide (Example 81A, 0.75 mL of 0.14 M in acetonitrile, 58 mg, 0.1 mmol) was added to a 20 mL vial followed by N,N-diisopropylethylamine (0.75 mL of 0.14 M in acetonitrile, 18 mg, 0.13 mmol). Subsequently, N-benzylbut-2-yn-1-amine (0.57 mL of 0.2 M in acetonitrile, 0.11 mmol) was added. The resulting mixture was shaken at room temperature overnight. It was then concentrated in vacuo and the residue was taken up in 1:1 MeOH/DMSO and purified by reverse phase HPLC (acetonitrile/water 0.1% TFA gradient elution method). 1H NMR (500 MHz, DMSO-d6/D2O) δ ppm 1.75 (3H) 2.24 (3H) 4.05 (2H) 4.55 (2H) 7.01-7.10 (1H) 7.17-7.29 (4H) 7.29-7.35 (1H) 7.40-7.54 (1H) 7.58-7.63 (1H) 7.66-7.94 (1H); MS (ESI+) m/z 506 (M+H)+. It was then concentrated in vacuo purified by reverse phase HPLC (acetonitrile/water 0.1% TFA gradient elution method)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of (Z)-3-methyl-1-(5-methyl-3-(2,2,3,3-tetrafluoro-2,3-dihydrobenzo[b][1,4]dioxin-6-yl)thiazol-2(3H)-ylidenecarbamoyl)-1H-imidazol-3-ium iodide (Example 81A, 0.75 mL of 0.14 M in acetonitrile, 58 mg, 0.1 mmol) was added to a 20 mL vial followed by N,N-diisopropylethylamine (0.75 mL of 0.14 M in acetonitrile, 18 mg, 0.13 mmol). Subsequently, N-benzylbut-2-yn-1-amine (0.57 mL of 0.2 M in acetonitrile, 0.11 mmol) was added. The resulting mixture was shaken at room temperature overnight. It was then concentrated in vacuo and the residue was taken up in 1:1 MeOH/DMSO and purified by reverse phase HPLC (acetonitrile/water 0.1% TFA gradient elution method). 1H NMR (500 MHz, DMSO-d6/D2O) δ ppm 1.75 (3 H) 2.24 (3 H) 4.05 (2 H) 4.55 (2 H) 7.01-7.10 (1 H) 7.17-7.29 (4 H) 7.29-7.35 (1 H) 7.40-7.54 (1 H) 7.58-7.63 (1 H) 7.66-7.94 (1 H); MS (ESI+) m/z 506 (M+H)+. It was then concentrated in vacuo purified by reverse phase HPLC (acetonitrile/water 0.1% TFA gradient elution method)