Efficient one-pot preparation of 5-substituted-2-amino-1,3,4-oxadiazoles using resin-bound reagents

Tetrahedron Letters

Volumn 45, Issue 16, 2004, Pages 3257-3260

  Coppo, Frank T ^a   Evans, Karen A ^a   Graybill, Todd L ^a   Burton, George ^a  

^a GLAXOSMITHKLINE   (United States)

Author keywords

1,3,4 Oxadiazole; 2 Amino 1,3,4 oxadiazole; Acylhydrazine; Acylthiosemicarbazide; Carbodiimide; Oxadiazole; Parallel synthesis; Solid supported reagents

Indexed keywords

OXADIAZOLE DERIVATIVE; RESIN;

ARTICLE; CHEMICAL PROCEDURES; CYCLIZATION; DRUG ISOLATION; DRUG PURIFICATION; DRUG SYNTHESIS;

EID: 1642603923     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.02.119     Document Type: Article

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24. Reagents were obtained from either the Aldrich Chemical Co., Lancaster Synthesis, or Alfa/Aesar Organics and used without further purification.
25. Marino, J. P.; Thompson, S. K.; Veber, D. F. SmithKline Beecham Corp. WO 02/078696 A1 (2002)
26. PS-Carbodiimide (Cat. no 800371, 1.1 mmol/g) was obtained from Argonaut Technologies, 1101 Chess Drive, Foster City, CA 94404.
27. 3-Aminopropyl functionalized silica gel (Aldrich, 1.0 mmol/g) was added to scavenge the excess isothiocyanate from the first step. PS-Bemp (Fluka, Cat. no 20026, 2.2 mmol/g) was added to scavenge any unreacted acylthiosemicarbazide, though this was typically not observed by LCMS.
28. 2O containing 0.02% TFA (3.6 min gradient) and monitored by a UV detector operating at 214 nm and by a SEDEX 75 evaporative light scattering detector (ELSD) operating at 42 °C. LCMS [M + H] signals were consistent with expected MW for all reported products.
29. 6-DMSO, 400 MHz): δ 10.38 (1H, s, NH), 8.59 (1H, d, J=2.0 Hz), 8.51 (1H, dd, J=4.8, 1.6 Hz), 7.76 (1H, dt, J=8.0, 2.0 Hz), 7.52 (2H, dt, J=8.0, 2.0 Hz), 7.40 (1H, ddd, J=8.0, 4.8, 0.8 Hz), 7.32 (2H, ddd, J=8.0, 2.0, 0.8 Hz), 6.97 (1H, app dt, J=7.2, 0.8 Hz), 4.24 (2H, s). LCMS [M + H] = 253.2, 1.28 in., 100% purity (UV 214 nm).
30. 1H NMR to confirm the purity assessment of the LCMS data.