3-cyclopropylprop-2-yn-1-amine

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

Procedure: Prepared in a similar manner to that described for Example 6 above, except using 2-[3-[2-(4-methyl-pyridin-2-yl)-vinyl]-1-(tetrahydro-pyran-2-yl)-1H-indazol-6-ylamino]-benzoic acid and 3-Cyclopropyl-prop-2-ynylamine. 1H NMR (DMSO-d6): δ 9.88 (1H, bs), 8.93 (1H, bt), 8.46 (1H, d, J=4.9 Hz), 8.08 (1H, d, J=8.7 Hz), 7.85 (1H, d, J=16.4 Hz), 7.69 (1H, d, J=7.6 Hz), 7.54–7.40 (5H, m), 7.14–7.11 (2H, m), 6.90 (1H, t, J=6.1 Hz), 5.81 (1H, d, J=7.5 Hz), 4.02 (2H, d, J=3.6 Hz), 3.95–3.85 (1H, m), 3.79–3.72 (1H, m), 2.49–2.35 (1H, m), 2.35 (3H, s), 2.15–2.01 (2H, m), 1.87–1.55 (3H, m), 1.30–1.25 (1H, m), 0.77–0.70 (2H, m), 0.59–0.54 (2H, m). Prepared in a similar manner to that

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

Procedure: Prepared-in a similar manner to that described for Example 6 above, except using 2-{3-[2-(4,6-Dimethyl-pyridin-2-yl)-vinyl]-1H-indazol-6-ylamino}-nicotinic acid p-toluene sulfonate and 3-Cyclopropyl-prop-2-ynylamine. 1H NMR (DMSO-d6): δ 13.01 (1H, s), 11.20 (1H, s), 9.19 (1H, bt), 8.51 (1H, s), 8.40 (1H, d, J=4.9 Hz), 8.15 (1H, d, J=7.5 Hz), 8.05 (1H, d, J=8.7 Hz), 7.83 (1H, d, J=16.4 Hz), 7.42 (1H, d, J=16.4 Hz), 7.31 (1H, s), 7.05 (1H, d, J=8.3 Hz), 6.96 (1H, s), 6.92 (1H, dd, J=7.5, 4.9 Hz), 4.06 (2H, d, J=4.14 Hz), 2.46 (3H, s), 2.29 (3H, s), 1.33–1.28 (1H, m), 0.77–0.72 (2H, m), 0.60–0.55 (2H, m).

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

Procedure: Was prepared in a similar manner to that described for Example 6 above, except using 2-[3-[2-(4,6-dimethyl-pyridin-2-yl)-vinyl]-1-(tetrahydro-pyran-2-yl)-1H-indazol-6-ylamino]-benzoic acid E and 3-Cyclopropyl-prop-2-ynylamine. 1H NMR (CDCl3): δ 9.51 (1H, s), 7.97 (1H, d, J=8.7 Hz), 7.81 (1H, d, J=16.6 Hz), 7.51–7.42 (3H, m), 7.34–7.29 (2H, m), 7.16 (1H, s), 7.11 (1H, dd, J=9.0,1.9 Hz), 6.85 (1H, s), 6.81 (1H, dt, J=7.2, 1.1 Hz), 6.23 (1H, t, J=7.2 Hz), 5.61 (1H, dd, J=9.0, 2.6 Hz), 4.17 (2H, dd, J=5.3, 2.3 Hz), 4.07–4.00 (1H, m), 3.75–3.66 (1H, m), 2.63–2.50 (1H, m), 2.54 (3H, s), 2.32 (3H, s), 2.20–2.02 (2H, m), 1.79–1.62 (3H, m), 1.29–1.19 (1H, m), 0.77–0.67 (4H, m). Was prepared in a similar manner to that

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

Procedure: To a solution of 3-cyclopropylprop-2-yn-1-amine (4.61 g) in ethanol (50 mL) was added 4-thioxo-1,3-thiazolidin-2-one (3.24 g), and the mixture was stirred at room temperature for 2 hr. The reaction mixture was concentrated, and the residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane) to give the title compound (4.20 g). The reaction mixture was concentrated the residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane)