1-(2-fluoroethyl)piperidin-4-amine

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

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

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: Prepared from 4-(1-(4-methoxybenzyl)-3-iodo-1H-pyrazolo[3,4-b]pyridin-4-yloxy)-3-fluorobenzenamine (245 mg, 0.500 mmol, prepared according to Example 7, Step B) and 1-(2-fluoroethyl)piperidin-4-amine (219 mg, 1.50 mmol) according to the procedure described for Example 138, Step C. Yield: 128 mg (50%). LRMS (APCI+): 100% purity, 220 nm, m/z 509 (M+1) detected.

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

Procedure: Prepared from 4-(1-(4-methoxybenzyl)-3-iodo-1H-pyrazolo[3,4-b]pyridin-4-yloxy)-3-fluorobenzenamine (245 mg, 0.500 mmol, prepared according to Example 7, Step B) and 1-(2-fluoroethyl)piperidin-4-amine (219 mg, 1.50 mmol) according to the procedure described for Example 138, Step C. Yield: 128 mg (50%). LRMS (APCI+): 100% purity, 220 nm, m/z 509 (M+1) detected.

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

Procedure: The title compound was prepared in accordance with the general method 4 described in example 16 from bis(trichloromethyl) carbonate, 1-(2-fluoro-ethyl)-piperidin-4-ylamine and (R)—N2-indan-1-yl-quinoline-2,6-diamine; MS: m/e=448.8 (M+H+).

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

Procedure: The title compound was prepared in accordance with the general method 4 described in example 16 from bis(trichloromethyl) carbonate, 1-(2-fluoroethyl)-piperidin-4-ylamine and rac-N2-(8-methoxy-1,2,3,4-tetrahydro-naphthalen-1-yl)-quinoline-2,6-diamine; MS: m/e=492.5 (M+H+).

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

Procedure: The title compound was prepared in accordance with the general method 4 described in example 16 from bis(trichloromethyl) carbonate, 1-(2-fluoroethyl)-piperidin-4-ylamine and rac-N2-(7-methoxy-indan-1-yl)-quinoline-2,6-diamine (Example 172); MS: m/e=478.7 (M+H+).

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of piperidin-4-yl-carbamic acid tert-butyl ester (2.00 g, 10.00 mmol), bromofluoroethane (1.5 g, 12.00 mmol) and potassium carbonate (2.80 g, 20.00 mmol) in acetonitrile (50 mL) was heated at 80° C. for 20 h. Cooled, diluted with ethyl acetate, washed with water, brine, dried over sodium sulfate and concentrated. The residue was dissolved in DCM (10 mL) and 4N HCl/dioxane (12 mL, 50.00 mmol) was added and the suspension was stirred for 20 h at ambient temperature. The solid was collected by filtration, washed well with ethyl acetate and dried in a vacuum oven to afford 1-(2-fluoro-ethyl)-piperidin-4-ylamine.HCl salt (1.70 g, 93%): 1H NMR (400 MHz, DMSO) δ 8.43 (s, 3H), 5.02-4.90 (m, 1H), 4.89-4.77 (m, 1H), 3.56-3.50 (m, 2H), 3.46 (d, J=3.7 Hz, 1H), 3.38 (d, J=3.8 Hz, 1H), 3.26 (d, J=4.9 Hz, 1H), 3.18-3.02 (m, 2H), 2.20-2.09 (m, 2H), 2.07-1.89 (m, 2H). Cooled washed with water, brine dried over sodium sulfate concentrated The residue was dissolved in DCM (10 mL) The solid was collected by filtration washed well with ethyl acetate dried in a vacuum oven