[Br:1][C:2]1[S:3][CH:4]=[C:5](C(O)=O)[N:6]=1.P(N=[N+]=[N-])([O:19][C:20]1C=CC=CC=1)(OC1C=CC=CC=1)=O.[N:29]1([CH2:35][C:36]2[N:41]=[C:40]([NH2:42])[CH:39]=[CH:38][CH:37]=2)[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1.CC#[N:45]>C(Cl)Cl>[Br:1][C:2]1[S:3][CH:4]=[C:5]([NH:45][C:20]([NH:42][C:40]2[CH:39]=[CH:38][CH:37]=[C:36]([CH2:35][N:29]3[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34]3)[N:41]=2)=[O:19])[N:6]=1To a stirred suspension of 2-bromothiazole-4-carboxylic acid (5.13 g, 2 mmol) in anhydrous CH3CN (40 ml) at RT, under N2, TEA (3.80 ml, 27 mmol) and (PhO)2PON3 (5.90 ml, 27 mmol) were added. The resulting solution was heated to 85° C. Upon reaching 85° C., a solution of 6-(piperidylmethyl)-2-pyridylamine (4.74 g, 25 mmol) in anhydrous CH3CN (60 ml) was added. The reaction was maintained at this temperature for 2.25 h. After cooling to RT the mixture was diluted with CH2Cl2 (50 ml) then washed with a saturated solution of NH4Cl(aq) (40 ml). The organic layer was separated, dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (3:1/2:1/1:1, EtOAc:acetone) to yield the title compound as a pale yellow solid. MS m/z: 396 (M+H), 398 (M+3). Calc'd for C15H18BrN50S: 395.04.
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