Acetic Anhydride → HCID 59263069, compound

HRID 881035Notes

Reaction equation

HRID 881035 reaction equation
[NH2:1][C:2](=[N:34]O)[C:3]1[CH:33]=[CH:32][C:6]([O:7][CH2:8][CH2:9][CH2:10][N:11]2[CH2:16][CH2:15][CH:14]([CH2:17][CH2:18][CH2:19][O:20][C:21]3[CH:30]=[CH:29][C:24]([C:25]([NH2:28])=[N:26]O)=[C:23]([F:31])[CH:22]=3)[CH2:13][CH2:12]2)=[CH:5][CH:4]=1.C(OC(=O)C)(=O)C>[C].[Pd].C(O)(=O)C>[NH2:34][C:2](=[NH:1])[C:3]1[CH:4]=[CH:5][C:6]([O:7][CH2:8][CH2:9][CH2:10][N:11]2[CH2:16][CH2:15][CH:14]([CH2:17][CH2:18][CH2:19][O:20][C:21]3[CH:30]=[CH:29][C:24]([C:25]([NH2:28])=[NH:26])=[C:23]([F:31])[CH:22]=3)[CH2:13][CH2:12]2)=[CH:32][CH:33]=1

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 72264646HCID 72264646, compound

Product 1

HCID 59263069HCID 59263069, compoundYield 82.2%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 176Acetic AcidSolvent

Procedure

To an acetic acid (2.0 mL) suspension of 56 mg of 4-{3-[1-(3-{4-[amino(hydroxyimino)methyl]phenoxy}propyl)-4-piperidinyl]propoxy}-2-fluoro-N′-hydroxybenzamidine was added 0.043 mL of acetic anhydride at room temperature, which was then stirred at the same temperature for one hour. To this mixture was added 5.0 mg of 5% palladium-carbon, which was then stirred under hydrogen atmosphere for 2 hours. Insoluble matter was filtered off, and the solvent was distilled off under reduced pressure. Thereto were added 6.0 mol/L hydrochloric acid and water, followed by distilling off the solvent under reduced pressure. The resultant residue was purified using silica gel column chromatography (silica gel: ODS-AM120-S50 from YMC, eluent; water). The resultant residue was dissolved in 5.0 mL of water, to which a 5.0 mol/L sodium hydroxide aqueous solution was then added to adjust the pH to 12.2. The solution was stirred under cooling with ice for 20 minutes, and the precipitate was collected by filtration to provide 43 mg of 4-{3-[1-(3-{4-[amino(imino)methyl]phenoxy}propyl)-4-piperidinyl]propoxy}-2-fluorobenzamidine as white solid form.

Workup

  1. stirringwas then stirred under hydrogen atmosphere for 2 hours
  2. filtrationInsoluble matter was filtered off
  3. distillationthe solvent was distilled off under reduced pressure
  4. additionThereto were added 6.0 mol/L hydrochloric acid and water
  5. distillationby distilling off the solvent under reduced pressure
  6. customThe resultant residue was purified
  7. dissolutionThe resultant residue was dissolved in 5.0 mL of water, to which a 5.0 mol/L sodium hydroxide aqueous solution
  8. additionwas then added
  9. stirringThe solution was stirred
  10. temperatureunder cooling with ice for 20 minutes
  11. filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record
ord-aaba581ab2c34741b72603f48db44d3e
Source dataset
uspto-grants-2015_03
Patent number
US08993603B2

Reaction notes

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