N-prop-2-ynylaniline

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: Following the procedure as described in Example 10, making variations as necessary to replace phenylacetylene with phenyl prop-2-ynyl amine to react with 2-azido-N-benzyl-4-methylthiazole-5-carboxamide, the title compound was obtained as a white solid in 18% yield: mp 159-162° C. (dichloromethane/hexanes); 1H NMR (300 MHz, CDCl3) δ 8.31 (s, 1H), 7.42-7.35 (m, 5H), 7.30-7.21 (m, 2H), 6.82-6.77 (m, 1H), 6.73-6.69 (m, 2H), 6.18 (t, J=6.0 Hz, 1H), 4.66 (d, J=6.0 Hz, 2H), 4.58 (d, J=6.0 Hz, 2H), 4.32 (br s, 1H), 2.70 (s, 3H); 13C NMR (75 MHz, CDCl3) 160.9, 155.4, 153.1, 147.7, 147.1, 137.4, 129.4, 128.9, 127.9, 127.9, 124.5, 119.3, 118.3, 113.1, 44.3, 39.6, 17.4; MS (ES+) m/z 405.3 (M+1).

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

Procedure: Following the procedure as described in Example 10, making variations as necessary to replace phenylacetylene with phenyl prop-2-ynyl amine to react with 2-azido-N-benzyl-4-methylthiazole-5-carboxamide, the title compound was obtained as a white solid in 18% yield: mp 159-162° C. (dichloromethane/hexanes); 1H NMR (300 MHz, CDCl3) δ 8.31 (s, 1H), 7.42-7.35 (m, 5H), 7.30-7.21 (m, 2H), 6.82-6.77 (m, 1H), 6.73-6.69 (m, 2H), 6.18 (t, J=6.0 Hz, 1H), 4.66 (d, J=6.0 Hz, 2H), 4.58 (d, J=6.0 Hz, 2H), 4.32 (br s, 1H), 2.70 (s, 3H); 13C NMR (75 MHz, CDCl3) 160.9, 155.4, 153.1, 147.7, 147.1, 137.4, 129.4, 128.9, 127.9, 127.9, 124.5, 119.3, 118.3, 113.1, 44.3, 39.6, 17.4; MS (ES+) m/z 405.3 (M+1).

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

Procedure: A solution of propargyl bromide (0.11 mL, 1 mmol) and aniline (0.46 mL, 5 mmol) in ethanol (2 mL) was stirred at room temperature for about 5 days. The solvent was concentrated under vacuum and the residue was purified by flash chromatography on silica gel using hexane/ethyl acetate (20:1) as eluent to provide Example 640. MS (ESI): m/z 132 (M+H)+. The solvent was concentrated under vacuum the residue was purified by flash chromatography on silica gel to provide Example 640

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

Procedure: A solution of propargyl bromide (0.11 mL, 1 mmol) and aniline (0.46 mL, 5 mmol) in ethanol (2 mL) was stirred at room temperature for about 5 days. The solvent was concentrated under vacuum and the residue was purified by flash chromatography on silica gel using hexane/ethyl acetate (20:1) as eluent to provide Example 640. MS (ESI): m/z 132 (M+H)+. The solvent was concentrated under vacuum the residue was purified by flash chromatography on silica gel to provide Example 640

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

Procedure: A solution of propargyl bromide (0.11 mL, 1 mmol) and aniline (0.46 mL, 5 mmol) in ethanol (2 mL) was stirred at room temperature for about 5 days. The solvent was concentrated under vacuum and the residue was purified by flash chromatography on silica gel using hexane/ethyl acetate (20:1) as eluent to provide Example 640. MS (ESI): m/z 132 (M+H)+. The solvent was concentrated under vacuum the residue was purified by flash chromatography on silica gel to provide Example 640