[Br:1][C:2]1[S:3][C:4]([CH2:10][CH3:11])=[CH:5][C:6]=1[C:7]([OH:9])=O.CN(C(ON1N=N[C:22]2[CH:23]=[CH:24][CH:25]=[N:26][C:21]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.N1CCCCC1>CN(C=O)C.O.C(#N)C>[Br:1][C:2]1[S:3][C:4]([CH2:10][CH3:11])=[CH:5][C:6]=1[C:7]([N:26]1[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]1)=[O:9]
2-Bromo-5-ethyl-thiophene-3-carboxylic acid (0.44 g, 1.88 mmol) was dissolved in DMF (10 mL). HATU (1.88 mmol) and piperidine (10 mmol) were added and the reaction mixture stirred for 3 hours. The mixture was diluted with water and acetonitrile and the product was purified by HPLC, eluting with 0%-95% acetonitrile in water (0.1% formic acid) over 30 minutes. The fractions containing the desired product were concentrated under vacuum to give the title compound (0.36 g). LCMS m/z 304.00 [M+H]+ RT=10.91 min (Analytical Method 2). 1H NMR (400 MHz, CHCl3-d): δ 6.6 (s, 1H), 3.7 (m, 2H), 3.35 (m, 2H), 2.75 (q, 2H), 1.65 (m, 4H), 1.55 (m, 2H), 1.27 (t, 3H).
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