These common heterocyclic compound, 563-83-7, name is Isobutyramide, 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. Application In Synthesis of Isobutyramide
A suspension of Example B7 (0.077 g, 0.888 mmol) in DCE (5.5 mL) was treated with oxalyl chloride (0.078 mL, 0.888 mmol), stirred at RT for 1 h, warmed to 80 C. for 1.5 h, cooled to RT, added drop-wise to a solution of 5-((2-(1-(trideuteromethyl)-1H-pyrazol-4-yl)pyridin-4-yl)oxy)pyridin-2-amine (0.200 g, 0.740 mmol) and pyridine (0.299 mL, 3.70 mmol) in THF (8 mL) and stirred at RT overnight. The mixture was treated with satd. Na2CO3, extracted with EtOAc (6*) and the combined organics were dried over Na2SO4, concentrated to dryness and purified via silica gel chromatography (MeOH/DCM). The material was dissolved in MeCN/H2O, frozen and lyophilized to afford N-((5-((2-(1-(trideuteromethyl)-1H-pyrazol-4-yl)pyridin-4-yl)oxy)pyridin-2-yl)carbamoyl)isobutyramide (199 mg, 70%) as a white solid. 1H NMR (400 MHz, DMSO-d6): delta 11.10 (s, 1H), 10.84 (s, 1H), 8.36 (d, J=5.7 Hz, 1H), 8.25-8.24 (m, 2H), 8.07 (d, J=9.0 Hz, 1H), 7.95 (d, J=0.7 Hz, 1H), 7.72 (dd, J=9.0, 2.9 Hz, 1H), 7.21 (d, J=2.4 Hz, 1H), 6.69 (dd, J=5.7, 2.4 Hz, 1H), 2.66 (m, 1H), 1.08 (d, J=6.8 Hz, 6H); MS (ESI) m/z: 384.2 (M+H+).
The synthetic route of Isobutyramide has been constantly updated, and we look forward to future research findings.
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;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics