5-PYRIDIN-2-YL-1,3,4-OXADIAZOL-2-YLAMINE synthesis
- Product Name:5-PYRIDIN-2-YL-1,3,4-OXADIAZOL-2-YLAMINE
- CAS Number:5711-72-8
- Molecular formula:C7H6N4O
- Molecular Weight:162.15
1452-63-7
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Yield:-
Reaction Conditions:
with water;potassium hydrogencarbonate in 1,4-dioxane; for 15 h;Inert atmosphere;Reflux;
Steps:
19 5.1.19. 2-[(2-Fluorobenzoyl)amino]-5-(pyridin-2-yl)-1,3,4-oxadiazole (83)
Picolinylhydrazide (5.0 g, 36.5 mmol, 1.0 equiv), cyanogen bromide (4.2 g, 40.1 mmol, 1.1 equiv), and potassium bicarbonate (4.0 g, 40.1 mmol, 1.1 equiv) in 1:1 dioxane-H2O (72 mL) were heated at reflux for 15 h. The reaction was cooled to rt and the suspension was filtered to collect the solid product, which was washed with 1:1 dioxane-H2O to afford crude 2-amino-5-(pyridin-2-yl)-1,3,4-oxadiazole (3.0 g, 51%) that was used in the next step without purification. A mixture of 2-fluorobenzoic acid (64 mg, 0.46 mmol, 1.3 equiv), CDI (85 mg, 0.52 mmol, 1.5 equiv) and DBU (0.10 mL, 0.67 mmol, 1.9 equiv) in DMF (1.5 mL) was stirred at 60 °C for 1 h. Next, crude 2-amino-5-(pyridin-2-yl)-1,3,4-oxadiazole prepared above (57 mg, 0.35 mmol, 1.0 equiv) was added and the reaction mixture was stirred at 60 °C for 17 h. The reaction was concentrated in vacuo onto silica gel. Purification by silica gel flash chromatography (linear gradient CH2Cl2 to 5% MeOH-CH2Cl2) afforded the title compound (72 mg, 72%) as a colorless solid: Rf = 0.55 (9:1 CH2Cl2-MeOH); 1H NMR (600 MHz, CDCl3) δ 7.24 (dd, J = 12.3, 8.8 Hz, 1H), 7.36 (t, J = 7.6 Hz, 1H), 7.46 (dd, J = 7.3, 5.0 Hz, 1H), 7.60-7.64 (m, 1H), 7.89 (t, J = 7.9 Hz, 1H), 8.21-8.24 (m, 2H), 8.77 (d, J = 4.7 Hz, 1H), 9.47 (s, 1H); 13C NMR (150 MHz, CDCl3) δ 116.5 (d, 2JC-F = 25 Hz), 118.9, 122.8, 125.5, 125.8, 132.8, 135.5 (d, 3JC-F = 9.2 Hz), 137.2, 143.1, 150.3, 157.5, 159.5, 160.7 (d, 1JC-F = 247 Hz), 160.8; HRMS (ESI+) calcd for C14H10FN4O2 [M+H]+ 285.0782, found 285.0775 (error 2.5 ppm).
References:
Meissner, Anja;Boshoff, Helena I.;Vasan, Mahalakshmi;Duckworth, Benjamin P.;Barry III, Clifton E.;Aldrich, Courtney C. [Bioorganic and Medicinal Chemistry,2013,vol. 21,# 21,p. 6385 - 6397]
13370-79-1
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5711-72-8
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