[CH3:1][N:2](C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)[CH3:3].[B-](F)(F)(F)F.CNC.[N+:26]([C:29]1[CH:30]=[N:31][CH:32]=[CH:33][C:34]=1[O:35][CH:36]1[CH2:41][CH2:40][CH:39]([C:42]([OH:44])=O)[CH2:38][CH2:37]1)([O-:28])=[O:27].CCN(C(C)C)C(C)C>C1COCC1>[CH3:1][N:2]([CH3:3])[C:42]([CH:39]1[CH2:38][CH2:37][CH:36]([O:35][C:34]2[CH:33]=[CH:32][N:31]=[CH:30][C:29]=2[N+:26]([O-:28])=[O:27])[CH2:41][CH2:40]1)=[O:44]
TBTU (630.0 mg, 1.962 mmol) and dimethylamine (1.784 mL of 2 M, 3.568 mmol) were added to a solution of 4-[(3-nitro-4-pyridyl)oxy]cyclohexanecarboxylic acid (475 mg, 1.784 mmol) and DIPEA (253.6 mg, 341.8 μL, 1.962 mmol) in THF (9.500 mL) and the resulting solution was stirred at RT overnight. The reaction mixture was partitioned between EtOAc and water, and the combined organic extracts were dried over MgSO4 and concentrated in vacuo. The residue was purified by column chromatography on silica eluting with 0-100% EtOAc/petroleum ether using the ISCO column companion system (12 g column) Clean fractions were combined and concentrated in vacuo to yield N,N-dimethyl-4-[(3-nitro-4-pyridyl)oxy]cyclohexanecarboxamide as a pale yellow oil. (180 mg, 34%). MS (ES+) 294.3.
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