ClCCl.[CH3:4][O:5][N:6]([CH3:14])[C:7]([C:9]1[CH:10]=[N:11][NH:12][CH:13]=1)=[O:8].[CH3:15][Si:16]([CH3:23])([CH3:22])[CH2:17][CH2:18][O:19][CH2:20]Cl.C(N(CC)C(C)C)(C)C>C(OCC)(=O)C>[CH3:4][O:5][N:6]([CH3:14])[C:7]([C:9]1[CH:13]=[N:12][N:11]([CH2:20][O:19][CH2:18][CH2:17][Si:16]([CH3:23])([CH3:22])[CH3:15])[CH:10]=1)=[O:8]A dichloromethane solution (3 mL) of N-methoxy-N-methyl-1H-pyrazole-4-carboxamide (142.7 mg, 2.68 mmol) was mixed with 2-(trimethysilyl)ethoxymethyl chloride (0.47 mL, 2.68 mmol) and N,N-diisopropylethylamine (0.94 mL, 5.36 mmol) and stirred at room temperature for 16 hours. After completion of the reaction, the reaction solution was mixed with ethyl acetate washed with saturated aqueous sodium chloride and the organic layer was dried over anhydrous sodium sulfate and evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1) to give the desired product (325.8 mg, 85% yield).
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