Potassium Carbonate → HCID 59519105, compound

Reaction equation

F[C:2]1[CH:3]=[CH:4][C:5]([N+:18]([O-:20])=[O:19])=[C:6]([CH:17]=1)[C:7]([NH:9][CH2:10][C:11](=[O:16])[NH:12][CH:13]([CH3:15])[CH3:14])=[O:8].[CH3:21][N:22]1[CH2:28][CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH:13]([NH:12][C:11]([CH2:10][NH:9][C:7](=[O:8])[C:6]1[CH:17]=[C:2]([N:25]2[CH2:26][CH2:27][CH2:28][N:22]([CH3:21])[CH2:23][CH2:24]2)[CH:3]=[CH:4][C:5]=1[N+:18]([O-:20])=[O:19])=[O:16])([CH3:15])[CH3:14]

Participants

Procedure

A mixture of 5-fluoro-N-(isopropylcarbamoylmethyl)-2-nitrobenzamide (INTERMEDIATE IV.1) (400 mg, 1.4 mmol), 1-methylhomopiperazine (0.20 mL, 1.6 mmol) and potassium carbonate (1 g) in acetonitrile (20 mL) were heated at reflux temperature under an Argon atmosphere for 16 h. The mixture was cooled, filtered, the residue washed with DCM (2×1 mL) and the volatiles evaporated under reduced pressure. The red coloured residue was dissolved in DCM (15 mL), washed with 1 N NaOH (aq.) (2×5 mL) and brine (1×5 mL), dried (Na2SO4) and concentrated under reduced pressure to afford N-(isopropylcarbamoylmethyl)-5-(4-methylperhydro-1,4-diazepin-1-yl)-2-nitrobenzamide (510 mg, 1.4 mmol, 100%) as an orange-red solid. This was used in the next step without further purification.