With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.3405-77-4,5-Methylisoxazole-3-carboxylic acid,as a common compound, the synthetic route is as follows.
5-Methylisoxazole-3-carboxylic acid (150 mg, 1.18 mmol) dissolved in toluene (2 mL) was treated with DMF (1 drop) and thionyl chloride (1.42 mmol, 103 Iota then heated to reflux for 5 h. The solvent was removed in vacuo to afford crude 5-methylisoxazole-3- carbonyl chloride (155 mg, 1.06 mmol) as a brown oil. The crude acid chloride without purification was dissolved in THF (4 mL), treated with Et3N (155 mu, i.o6 mmol) and stirred for 5 min, before adding 4-(2-aminoethyl)benzenesulfonamide (220 mg, 1.10 mmol) and stirring at room temperature for 15 h under N2 atmosphere. The reaction mixture was concentrated in vacuo and purified by MPLC, affording the titled compound as an amorphous white solid (205 mg, 62%): NMR (600 MHz, DMSO- d6) delta 8.79 (t, J = 5-8 Hz, lH), 7-74 (d, J = 8.3 Hz, 2H), 7.41 (d, J = 8.3 Hz, 2H), 7.30 (s, 2H), 6.50 (q, J= 0.8 Hz, lH), 3.49 (m, 2H), 2.91 (t, J = 7.2 Hz, 2H), 2.45 (d, J= 0.8 Hz, 3H); ^C NMR (151 MHz, DMSO-d6) delta 171.0, 158.8, 158.5, 143-3, 142.0, 129.0, 125. 6, 101.1, 39-8, 34-3, H-7; HRMS (ESI-TOF) m/z calcd for C13H14N304S [M-H]- 308.0711, found 308.0708; LC-MS m/z 308.0 [M+H]+, purity >99% (ELSD).
The synthetic route of 3405-77-4 has been constantly updated, and we look forward to future research findings.
Reference£º
Patent; THE UNIVERSITY OF QUEENSLAND; THE PROVOST, FELLOWS, FOUNDATION SCHOLARS, AND THE OTHER MEMBERS OF BOARD, OF THE COLLEGE OF THE HOLY AND UNDIVIDED TRINITY OF QUEEN ELIZABETH NEAR DUBLIN; O’NEILL, Luke; COLL, Rebecca; COOPER, Matthew; ROBERTSON, Avril; SCHRODER, Kate; MACLEOD, Angus Murray; MILLER, David John; (109 pag.)WO2018/215818; (2018); A1;,
Isoxazole – Wikipedia
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