Potassium Carbonate → HCID 59519105, compound

HRID 1161849Notes

Reaction equation

HRID 1161849 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

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2283491-MethylhomopiperazineHCID 44203076HCID 44203076, compound

Product 1

HCID 59519105HCID 59519105, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

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.

Workup

  1. temperaturewere heated
  2. temperatureat reflux temperature under an Argon atmosphere for 16 h
  3. temperatureThe mixture was cooled
  4. filtrationfiltered
  5. washthe residue washed with DCM (2×1 mL)
  6. customthe volatiles evaporated under reduced pressure
  7. dissolutionThe red coloured residue was dissolved in DCM (15 mL)
  8. washwashed with 1 N NaOH (aq.) (2×5 mL) and brine (1×5 mL)
  9. dry with materialdried (Na2SO4)
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-84d5c5e449234e64b23ae00102024938
Source dataset
uspto-grants-2010_10
Patent number
US07820649B2

Reaction notes

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