Ethanol → HCID 178456333, compound

HRID 80897Notes

Reaction equation

HRID 80897 reaction equation
[CH:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]2[N:15]=[CH:14][C:13]([C:16]3[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[CH:18][CH:17]=3)=[CH:12][CH:11]=2)[CH2:6][CH2:5]1)([CH3:3])[CH3:2].C(O)C.Cl.[NH2:28][OH:29].C(=O)([O-])[O-].[K+].[K+]>O>[OH:29][NH:28][C:20](=[NH:21])[C:19]1[CH:18]=[CH:17][C:16]([C:13]2[CH:14]=[N:15][C:10]([N:7]3[CH2:8][CH2:9][N:4]([CH:1]([CH3:2])[CH3:3])[CH2:5][CH2:6]3)=[CH:11][CH:12]=2)=[CH:23][CH:22]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 11430Potassium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 58006673HCID 58006673, compound

Product 1

HCID 178456333HCID 178456333, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4-(6-(4-isopropylpiperazin-1-yl)pyridin-3-yl)benzonitrile (330 mg, 1.1 mmol, prepared as described in Example 10), ethanol (15 mL), hydroxylamine hydrochloride (225 mg, 3.2 mmol), potassium carbonate (240 mg, 1.7 mmol) and water (1.5 mL) was stirred at reflux temperature overnight. The reaction mixture was allowed to cool to rt, and the solid was isolated by filtration and dried. The solid was then stirred with water (10 mL) to remove inorganic residues. The mixture was filtered and the solid was washed with water and a small portion of ethanol. Drying in vacuo afforded 260 mg (71%) of N-hydroxy-4-(6-(4-isopropylpiperazin-1-yl)pyridine-3-yl)benzamidine.

Workup

  1. temperatureat reflux temperature overnight
  2. customthe solid was isolated by filtration
  3. customdried
  4. stirringThe solid was then stirred with water (10 mL)
  5. customto remove inorganic residues
  6. filtrationThe mixture was filtered
  7. washthe solid was washed with water
  8. customDrying in vacuo

Sources & evidence

ORD record
ord-0802f14f732e41278f0330394a1ce505
Source dataset
uspto-grants-2014_09
Patent number
US08846677B2

Reaction notes

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