With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.344329-76-6,Tetrahydro-2H-pyran-4-carboxamide,as a common compound, the synthetic route is as follows.
Example 117 A mixture of Example B5 (66 mg, 0.508 mmol) in DCE (2 mL) was treated with oxalyl chloride (64 mg, 0.508 mmol), stirred at RT for 5 min, then warmed to 80¡ã C. for 45 min. The mixture was cooled to RT, added to a solution of DIEA (188 mg, 1.456 mmol) and Example A25 (100 mg, 0.339 mmol) in dioxane (4 mL) and stirred at RT for 3 h. The mixture was diluted with EtOAc, washed successively with satd. NaHCO3, 1N NaOH and brine, dried over Na2SO4, concentrated to dryness and purified via reverse-phase silica gel chromatography (MeCN/H2O with 0.1percent TFA). The pure fractions were partially evaporated under reduced pressure and the aqueous residue was neutralized with satd. NaHCO3 and extracted with EtOAc (3*). The combined organics were washed with brine, dried over Na2SO4 and concentrated to dryness to afford N-((4,6-dimethyl-5-((2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yl)oxy)pyridin-2-yl)carbamoyl)tetrahydro-2H-pyran-4-carboxamide (29 mg, 19percent) as a white solid. 1H NMR (400 MHz, DMSO-d6): delta 10.95 (s, 1H), 10.86 (s, 1H), 8.33 (d, J=5.7 Hz, 1H), 8.25 (s, 1H), 7.95 (s, 1H), 7.84 (s, 1H), 7.11 (d, J=2.4 Hz, 1H), 6.51 (dd, J=5.7, 2.5 Hz, 1H), 3.90-3.85 (m, 2H), 3.84 (s, 3H), 3.30-3.27 (m, 2H), 2.73-2.65 (m, 1H), 2.18 (s, 3H), 2.10 (s, 3H), 1.74-1.68 (m, 2H), 1.65-1.55 (m, 2H); MS (ESI) m/z: 451.2 (M+H+).
344329-76-6, 344329-76-6 Tetrahydro-2H-pyran-4-carboxamide 13197203, aTetrahydropyrans compound, is more and more widely used in various fields.
Reference£º
Patent; Deciphera Pharmaceuticals, LLC; Flynn, Daniel L.; Caldwell, Timothy Malcolm; Kaufman, Michael D.; Patt, William C.; Samarakoon, Thiwanka; Vogeti, Lakshminarayana; Yates, Karen M.; US2014/275080; (2014); A1;,
Tetrahydropyran – Wikipedia
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