[CH3:1][O:2][CH2:3][CH2:4][NH:5][C:6]1[C:7]([CH3:19])=[C:8]([CH:12]=[CH:13][C:14]=1[S:15]([CH3:18])(=[O:17])=[O:16])[C:9]([OH:11])=O.[OH:20][C:21]1[N:25]([CH3:26])[N:24]=[C:23]([CH:27]2[CH2:29][CH2:28]2)[CH:22]=1.[CH3:30]CN=C=NCCCN(C)C.CCN(CC)CC.[Si](C#N)(C)(C)C.[C-]#N.[K+]>CC#N>[CH:27]1([C:23]2[C:22]([C:9]([C:8]3[CH:12]=[CH:13][C:14]([S:15]([CH3:18])(=[O:17])=[O:16])=[C:6]([N:5]([CH2:4][CH2:3][O:2][CH3:1])[CH3:30])[C:7]=3[CH3:19])=[O:11])=[C:21]([OH:20])[N:25]([CH3:26])[N:24]=2)[CH2:29][CH2:28]1Under nitrogen, 0.59 g of crude 3-[(2-methoxyethyl)amino]-2-methyl-4-(methylsulfonyl)benzoic acid was dissolved in 30 ml of CH3CN, and 0.35 g (3 mmol) of 5-hydroxy-3-cyclopropyl-1-methylpyrazole and 0.45 g (2 mmol) of EDAC were then added. The mixture was stirred at RT for one day. 0.36 g (4 mmol) of NEt3, 0.08 g (1 mmol) of Me3SiCN and a spatula tip of KCN were then added, and the mixture was stirred at RT for two days. The mixture was then concentrated, and the residue was taken up in 100 ml of CH2Cl2 and washed with 10% strength H2SO4. The organic phase was dried over MgSO4, concentrated and the residue was purified chromatographically (SiO2, EA/n-heptane=1:1+5% acetic acid). This gave a brown oil.
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