methyl 2-(2-morpholin-4-ylethylamino)acetate

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: A solution of (2-Morpholin-4-yl-ethylamino)acetic acid methyl ester (0.40 g, 2.0 mmol) and triethylamine (1.0 mL, 7.11 mmol) in DMF (20 mL) was treated with 5-bromo-3-bromomethyl-pyridin-2-ylamine hydrobromide (0.70 g, 2.0 mmol). After stirring at room temperature under for 7 h, the cloudy mixture was diluted with H2O (50 mL) and then extracted with EtOAc (4×50 mL). The combined organic layers were washed with H2O (3×50 mL) and brine (50 mL), dried over Na2SO4, filtered and the solvent was removed in vacuo. Purification by flash column chromatography (silica gel, CH2Cl2/MeOH, 98:2 to 96:4) gave the title compound (0.46 g, 60%) as a colorless oil: MS (ESI) m/e 387 (M+H)+. extracted with EtOAc (4×50 mL) The combined organic layers were washed with H2O (3×50 mL) and brine (50 mL) dried over Na2SO4 filtered the solvent was removed in vacuo Purification by flash column chromatography (silica gel, CH2Cl2/MeOH, 98:2 to 96:4)

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

Procedure: A solution of [tert-butoxycarbonyl-(2-morpholin-4-yl-ethyl)amino]acetic acid methyl ester (0.79 g, 2.61 mmol) in CH2Cl2 (10 mL) was treated with TFA (10 mL). After stirring at room temperature for 1 h, the solution was concentrated in vacuo. The oil was dissolved in CH2Cl2 (50 mL) and the resulting solution was washed with saturated aqueous NaHCO3 (50 mL). The aqueous layer was extracted with CH2Cl2 (10×50 mL). The combined organic layers were dried over Na2SO4, filtered and the solvent was removed in vacuo to give the title compound (0.40 g, 76%) as a yellow oil: 1H NMR (300 MHz, CDCl3) δ 3.69-3.74 (m, 7H), 3.45 (s, 2H), 2.69-2.73 (m, 2H), 2.45-2.52 (m, 6H), 1.84 (s, 1H). the solution was concentrated in vacuo The oil was dissolved in CH2Cl2 (50 mL) the resulting solution was washed with saturated aqueous NaHCO3 (50 mL) The aqueous layer was extracted with CH2Cl2 (10×50 mL) The combined organic layers were dried over Na2SO4 filtered the solvent was removed in vacuo