Melting points

of the synthesized www.selleckchem.com/products/PD-0332991.html Compounds were determined in open capillaries on a Büchi B-540 melting point apparatus and are uncorrected. Reactions were monitored by thin-layer https://www.selleckchem.com/products/CAL-101.html chromatography (TLC) on silica gel 60 F254 aluminum sheets. The mobile phase was ethanol:ethyl acetate, 1:1, and detection was made using UV light. FT-IR spectra were recorded as potassium bromide pellets using a Perkine Elmer 1600 series FTIR spectrometer. 1H NMR and 13C NMR spectra were registered on DMSO-d 6 on a BRUKER AVENE II 400 MHz NMR Spectrometer (400.13 MHz for 1H and 100.62 MHz for 13C). The chemical shifts are given in ppm relative to Me4Si as an internal reference; J values are given in Hz. The elemental analysis was performed on a Costech Elemental Combustion System CHNS-O elemental analyzer. All the compounds selleck gave C, H, and N analysis results within ±0.4 % of the theoretical values. The mass spectra were obtained on a Quattro LC–MS (70 eV) Instrument. Compounds 1 and 2 are available commercially. Synthesis of compound 3 Ethylbromoacetate (10 mmol) was added to the mixture

of compound 2 (10 mmol), and triethylamine (10 mmol) was added dropwise in dry tetrahydrofurane at 0–5 °C. Then, the reaction content was allowed to reach to room temperature and stirred for 11 h (the progress of the reaction was monitored by TLC). The precipitated triethylammonium salt was removed by filtration. After evaporating the solvent under reduced pressure, a brown solid appeared. This crude product was recrystallized from ethanol–water Protirelin (1:2) to afford the desired product. Ethyl N-(6-morpholin-4-ylpyridin-3-yl)glycinate (2) Yield (1.27 g, 50 %);

m.p. 83–84 °C; IR (KBr, ν, cm−1): 3,378 (NH), 1,725 (C=O), 1,575 (C=N), 1,118 (C–O); 1H NMR (DMSO-d 6, δ ppm): 1.17 (t, 3H, CH3, J = 7.4 Hz), 3.18 (t, 4H, 2NCH2, J = 4.8 Hz), 3.69 (t, 4H, 2OCH2, J = 4.4 Hz), 3.84 (d, 2H, NHCH2, J = 6.4 Hz), 4.08 (q, 2H, OCH 2 CH3, J = 7 Hz), 5.57 (t, 1H, NH, J = 6.8 Hz), 6.67 (d, 1H, arH, J = 9 Hz), 6.92–6.98 (m, 1H, arH), 7.56 (d, 1H, arH, J = 2.4 Hz); 13C NMR (DMSO-d 6, δ ppm): 14.83 (CH3), 45.84 (NHCH2), 47.40 (2NCH2), 60.94 (CH 2 OCH3), 66.74 (2OCH2), arC: [108.94 (CH), 123.74 (CH), 132.35 (CH), 138.22 (C), 153.34 (C)], 172.08 (C=O); LC–MS: m/z (%) 266.257 [M+1]+ (85), 164.12 (94); Anal.calcd (%) for C13H19N3O3 : C, 58.85; H, 7.22; N, 15.84. Found: C, 58.65; H, 7.28; N, 15.85. Synthesis of compound 4 Hydrazide hydrate (25 mmol) was added to the solution of compound 2 (10 mmol) in absolute ethanol, and the mixture was allowed to reflux for 7 h. On cooling the reaction mixture to room temperature, a white solid appeared. The crude product was filtered off and recrystallized from ethanol to give the desired compound 4. 2-[6-(Morpholin-4-yl)pyridin-3-ylamino]acetohydrazide (4) Yield (2.23 g, 89 %); m.p.