3-methoxy-4-(1-methylpiperidin-4-yl)aniline

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

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

Procedure: To a mixture of benzyl [3-methoxy-4-(1-methylpiperidin-4-yl)phenyl]carbamate (Preparation Example 464) (1.26 g), ethanol (20 mL) and THF (10 mL), 5% palladium on carbon (0.38 g) was added and stirred overnight at room temperature under a hydrogen atmosphere at normal pressure. After filtration through celite, the filtrate was distilled off under reduced pressure to give 3-methoxy-4-(1-methylpiperidin-4-yl)aniline (0.80 g) as a light pink solid. was added After filtration through celite the filtrate was distilled off under reduced pressure

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

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

Procedure: Trifluoro-methanesulfonic acid 7-(6-methoxy-pyridin-3-yl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl ester (0.138 g, 0.369 mmol) and 3-Methoxy-4-(1-methyl-piperidin-4-yl)-phenylamine (0.102 g, 0.461 mmol) were reacted in an analogous manner to Example 908D at room temp for 72 h. The reaction mixture was concentrated, taken up in EtOAc, and washed with brine. The EtOAc layer was dried, filtered over MgSO4, and concentrated. The resulting residue was purified by Gilson RP-HPLC and lyophilized. HPLC rt=2.455 min, purity=98%, LCMS=445.0 (M+H). 1H NMR (400 MHz, (D3C)2SO, δ, ppm): 9.47 (s, 1H), 9.29 (bs, 1H), 9.02 (s, 1H), 8.99 (d, 1H), 7.47 (s, 1H0, 7.23 (d, J=7.5 Hz, 1H), 7.17 (d, J=4.8 Hz, 1H), 7.03 (d, J=8.2 Hz, 1H), 7.17 (d, J=4.8 Hz, 1H), 7.03 (d, J=8.2 Hz, 1H), 6.98 (s, 1H), 6.96 A (d, J=4.1 Hz, 1H), 3.93 (s, 3H), 3.71 (s, 3H), 3.49 (d, J=11.7 Hz, 2H), 3.11-3.05 (m, 3H), 2.80 (d, J=4.0 Hz, 3H), 1.95-1.76 (m, 4H). The reaction mixture was concentrated washed with brine The EtOAc layer was dried filtered over MgSO4 concentrated The resulting residue was purified by Gilson RP-HPLC HPLC rt=2.455 min, purity=98%, LCMS=445.0 (M+H)

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

Procedure: To a mixture of benzyl [3-methoxy-4-(1-methylpiperidin-4-yl)phenyl]carbamate (Preparation Example 464) (1.26 g), ethanol (20 mL) and THF (10 mL), 5% palladium on carbon (0.38 g) was added and stirred overnight at room temperature under a hydrogen atmosphere at normal pressure. After filtration through celite, the filtrate was distilled off under reduced pressure to give 3-methoxy-4-(1-methylpiperidin-4-yl)aniline (0.80 g) as a light pink solid. was added After filtration through celite the filtrate was distilled off under reduced pressure