These common heterocyclic compound, 5511-18-2, name is Adamantane-1-carboxamide, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. 5511-18-2
Example 37 A solution of Example B13 (0.150 g, 0.837 mmol) in dioxane (10 mL) was treated with oxalyl chloride (0.150 g, 1.182 mmol), heated at 100 C. for 2 h, cooled to RT and concentrated to dryness. The residue was treated with a solution of Example A6 (0.150 g, 0.533 mmol) and pyridine (0.080 g, 1.011 mmol) in DCM (10 mL) and stirred at RT for 2 days. The mixture was concentrated to dryness, the residue treated with MeCN and the resulting solid collected via filtration and dried to afford N-((6-methyl-5-((2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yl)oxy)pyridin-2-yl)carbamoyl)adamantane-1-carboxamide (200 mg, 77%) as a white solid. 1H NMR (400 MHz, DMSO-d6): delta 11.18 (s, 1H), 10.32 (s, 1H), 8.35 (d, J=5.7 Hz, 1H), 8.24 (s, 1H), 7.95 (d, J=0.7 Hz, 1H), 7.90 (s, 1H), 7.61 (d, J=8.8 Hz, 1H), 7.16 (d, J=2.4 Hz, 1H), 6.60 (dd, J=5.7, 2.4 Hz, 1H), 3.83 (s, 3H), 2.25 (s, 3H), 1.98 (m, 3H), 1.89 (m, 6H), 1.66 (m, 6H); MS (ESI) m/z: 487.2 (M+H+).
Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 5511-18-2.
Reference:
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;,
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