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 83 A solution of Example B5 (58 mg, 0.447 mmol) in DCE (1.5 mL) was treated drop-wise with oxalyl chloride (42 muL, 0.484 mmol), stirred at RT for 0.5 h, then heated at 80¡ã C. for 1 h. The mixture was cooled to RT, treated with a mixture of Example A17 (110 mg, 0.372 mmol) and pyridine (147 mg, 1.862 mmol) in THF (3 mL) and stirred at RT for 2 h. The mixture was treated with EtOAc, washed with satd. NaHCO3, then brine, dried over Na2SO4, concentrated to dryness and purified via silica gel chromatography (MeOH/EtOAc). The material was re-purified via reverse-phase silica gel chromatography (MeCN/H2O with 0.1percent TFA). The pure fractions were concentrated under reduced pressure and the aqueous material neutralized with satd. NaHCO3. The material was extracted with EtOAc (3*) and the combined organics were washed with brine, dried over Na2SO4 and concentrated to dryness to afford N-((6-ethyl-5-((2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yl)oxy)pyridin-2-yl)carbamoyl)tetrahydro-2H-pyran-4-carboxamide (22 mg, 13percent) as a white solid. 1H NMR (400 MHz, DMSO-d6): delta 11.02 (s, 1H), 10.88 (s, 1H), 8.36 (d, J=5.7 Hz, 1H), 8.26 (s, 1H), 7.96 (d, J=0.7 Hz, 1H), 7.92 (d, J=8.8 Hz, 1H), 7.63 (d, J=8.8 Hz, 1H), 7.18 (d, J=2.4 Hz, 1H), 6.61 (dd, J=5.7, 2.5 Hz, 1H), 3.89 (d, J=11.3 Hz, 2H), 3.84 (s, 3H), 3.32 (s, 2H), 2.70-2.64 (m, 1H), 2.59 (q, J=7.5 Hz, 2H), 1.73 (d, J=13.0 Hz, 2H), 1.64-1.62 (m, 2H), 1.12 (t, J=7.5 Hz, 3H); MS (ESI) m/z: 451.2 (M+H+).
344329-76-6, As the paragraph descriping shows that 344329-76-6 is playing an increasingly important role.
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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