Synthesis and structure–activity relationships of isoxazole carboxamides as growth hormone secretagogue receptor antagonists

Z Xin, H Zhao, MD Serby, B Liu, VG Schaefer…

Index: Xin, Zhili; Zhao, Hongyu; Serby, Michael D.; Liu, Bo; Schaefer, Verlyn G.; Falls, Douglas H.; Kaszubska, Wiweka; Colins, Christine A.; Sham, Hing L.; Liu, Gang Bioorganic and Medicinal Chemistry Letters, 2005 , vol. 15, # 4 p. 1201 - 1204

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Citation Number: 24

Abstract

... Reagents and conditions: (a) CDI, MeCN, then potassium ethyl malonate, Et 3 N, MgCl 2 , 38–64%; (b) N-hydroxyarylcarboximidoyl chloride, NaOMe, MeOH, rt, 59–73%; (c) NaOH, MeOH, H 2 O, 100%; (d) amines, TBTU or HATU, DIPEA, DMF, rt, 78–92%; (e) 2-aminobenzoic acid allyl ester, NaHCO 3 , THF, rt, 49%; (f) Pd(PPh 3 ) 4 , morpholine, dichloromethane, rt, 100%. ... The substitution on meta-position (3f–g) seemed to be less favorable. ... 1, H, H, 0.13, 0.18. ...