[N+:1]([C:4]1[CH:5]=[N:6][N:7]([CH2:9][CH2:10][C:11]([OH:13])=O)[CH:8]=1)([O-:3])=[O:2].C(N(C(C)C)CC)(C)C.[NH:23]1[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1.ON1C2C=CC=CC=2N=N1.CN(C)CCCN=C=NCC.C(=O)(O)[O-].[Na+]>CN(C=O)C>[N+:1]([C:4]1[CH:5]=[N:6][N:7]([CH2:9][CH2:10][C:11]([N:23]2[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]2)=[O:13])[CH:8]=1)([O-:3])=[O:2]To a solution of 3-(4-nitro-1H-pyrazol-1-yl)propanoic acid (4.4 mmol) in 5 mL DMF were added diisopropylethylamine (1.2 mL, 1.5 eq), piperidine (0.66 mL, 1.5 eq), 1-hydroxybenzotriazole (0.90 g, 1.5 eq) and N-(3-Dimethylaminopropyl)-N′-ethylcarbodiimide (1.27 g, 1.5 eq). After stirring at rt for 17 h, saturated sodium bicarbonate was added and the aqueous phase extracted with DCM. The combined organic phases were dried over sodium sulfate and evaporated to afford 3-(4-nitro-1H-pyrazol-1-yl)-1-(piperidin-1-yl)propan-1-one in quantitative yield.
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