2-propoxyethanamine

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

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

Procedure: This compound was prepared from ethyl 1-[2-(dimethylamino)-2-oxoethyl]-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate and [2-(propyloxy)ethyl]amine employing methods similar to those described in Example 245 and was purified by reverse phase preparative BPLC (C-18 stationary phase; 10-100% CH3CN/water/0.1% formic acid mobile phase). The product was obtained as a white solid: 1H NMR (d6-DMSO) δ 10.63 (1H, br), 8.21 (1H, br s), 7.30 (1H, br s), 7.28 (2H, dd, J˜9, 5.6 Hz), 7.11 (2H, t, J˜9 Hz), 4.95 (2H, s), 4.01 (2H, s), 3.43-3.30 (6H, m), 3.08 (3H, s), 2.79 (3H, s), 1.50 (2H, m, J=7 Hz), 0.85 (3H, t, J=7 Hz); HRMS calcd for C25H29FN4O5+H+: 485.2200. Found: 485.2190. was purified by reverse phase preparative BPLC (C-18 stationary phase; 10-100% CH3CN/water/0.1% formic acid mobile phase) The product was obtained as a white solid

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

Procedure: This compound was prepared from ethyl 1-[2-(dimethylamino)-2-oxoethyl]-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate and [2-(propyloxy)ethyl]amine employing methods similar to those described in Example 245 and was purified by reverse phase preparative BPLC (C-18 stationary phase; 10-100% CH3CN/water/0.1% formic acid mobile phase). The product was obtained as a white solid: 1H NMR (d6-DMSO) δ 10.63 (1H, br), 8.21 (1H, br s), 7.30 (1H, br s), 7.28 (2H, dd, J˜9, 5.6 Hz), 7.11 (2H, t, J˜9 Hz), 4.95 (2H, s), 4.01 (2H, s), 3.43-3.30 (6H, m), 3.08 (3H, s), 2.79 (3H, s), 1.50 (2H, m, J=7 Hz), 0.85 (3H, t, J=7 Hz); HRMS calcd for C25H29FN4O5+H+: 485.2200. Found: 485.2190. was purified by reverse phase preparative BPLC (C-18 stationary phase; 10-100% CH3CN/water/0.1% formic acid mobile phase) The product was obtained as a white solid

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

Procedure: The title compound, white solid, m.p. 77.8-78.9° C. and MS: m/e=297 (M+) was prepared in accordance with the general method of example 1 from diphenylacetyl chloride and 2-propoxy-ethylamine.