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acetate. The combined ethyl acetate extracts were dried, fil-
tered and evaporated under reduced pressure to afford a grey
gum, which was purified with column chromatography eluting
with (chloroform/methanol) (95/5) to afford (8.0 mg, 72.2%)
the desired 5-(3-(3-(naphthalene-2-ylmethyl)-1,2,4-oxadiazol-
5-yl)-1H-indol-1-yl)pentanoic acid (59) as a grey gum. M.S.
m/z 426 (M þ 1)þ. 1H NMR (MeOH-d4) D 0.9 (2H, m,
CH2), 1.62 (2H, m, CH2), 1.92 (2H, m, CH2), 2.3 (2H, m,
CH2), 4.58 (2H, s, CH2), 7.25e7.31 (4H, m, 4 ꢃ ArH),
7.46e7.51 (2H, m, 2 ꢃ ArH), 7.52e7.55 (4H, m, 4 ꢃ ArH),
7.82 (2H, d, J ¼ 8.1 Hz, 2 ꢃ ArH), 7.88 (2H, d, J ¼ 8.7 Hz,
2 ꢃ ArH), 8.11 (1H, m, ArH), 8.13 (1H, s, ArH), 8.22 (1H,
m, ArH). H.p.l.c. retention time ¼ 2.53 min; (100% B)
(B ¼ 90% CH3CN/10% H2O).
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drous DMF (10.0 mL) and sodium hydride (60% dispersion,
437.6 mg, 11.4 mmol) was added and the reaction mixture
was stirred at room temperature for 30 min. After this 4-(2-
chloroethyl)morpholine hydrochloride (1.06 g, 5.7 mmol)
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der the atmosphere of nitrogen for 18 h. After this the reaction
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was evaporated under reduced pressure to afford a purple
gum, which was purified with column chromatography eluting
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1
M.S. m/z 189 (M þ 1)þ. H NMR (DMSO-d6) D 2.41 (4H, t,
J ¼ 4.5 Hz, 2 ꢃ CH2), 2.48 (2H, t, J ¼ 6.0 Hz, CH2), 3.55
(4H, t, J ¼ 4.5 Hz, 2 ꢃ CH2), 3.66 (2H, t, J ¼ 6.0 Hz, CH2),
7.24 (2H, m, 2 ꢃ ArH), 7.69 (2H, m, 2 ꢃ ArH), 8.44 (1H, s,
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Acknowledgement
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The authors acknowledge the support of AMRAD and the
Australian Research Council.
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