Nitrogen → HCID 18414393, compound

HRID 1978049Notes

Reaction equation

HRID 1978049 reaction equation
N#N.CC1[N:5]([C:10]2[CH:15]=[C:14]([CH3:16])[CH:13]=[C:12]([C:17]3[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][N:25]4[CH2:30][CH2:29][N:28]([CH2:31][CH2:32][C:33]5[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=5)[CH2:27][CH2:26]4)=[CH:19][CH:18]=3)[N:11]=2)C(C)=CC=1.Cl.NO.[2H]C(Cl)(Cl)Cl.CO[2H]>CCOCC.C(O)C.O>[CH2:31]([N:28]1[CH2:27][CH2:26][N:25]([CH2:24][CH2:23][C:20]2[CH:21]=[CH:22][C:17]([C:12]3[N:11]=[C:10]([NH2:5])[CH:15]=[C:14]([CH3:16])[CH:13]=3)=[CH:18][CH:19]=2)[CH2:30][CH2:29]1)[CH2:32][C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1

Participants

8

Reactant 4

HCID 947NitrogenHCID 443297Hydroxyamine hydrochlorideHCID 21995390HCID 21995390, compoundHCID 131722572HCID 131722572, compound

Product 1

HCID 18414393HCID 18414393, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

To a 100 mL three-necked round-bottomed flask equipped with septum and N2 inlet were added 165 mg (0.345 mmol) 2-(2,5-dimethylpyrrol-1-yl)-4-methyl-6-(4-(2-(phenethylpiperazin-4-yl)ethyl)phenyl)-pyridine, 120 mg (1.726 mmol) hydroxylamine hydrochloride, 1 mL water, and 5 mL ethanol. The reaction was refluxed 14 hr, cooled, evaporated, and taken up in ethyl acetate. The organic layer was washed with water and brine, dried over sodium sulfate, and evaporated. The residue was chromatographed on silica gel usirg methanol/methylene chloride as eluant to afford an oil, which was converted to thie hydrochloride salt using 1 N HCl in ether to give 18 mg (10%), mp 242-250° C.

Workup

  1. temperatureThe reaction was refluxed 14 hr
  2. temperaturecooled
  3. customevaporated
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over sodium sulfate
  6. customevaporated
  7. customThe residue was chromatographed on silica gel usirg methanol/methylene chloride as eluant
  8. customto afford an oil, which
  9. customto give 18 mg (10%), mp 242-250° C.

Sources & evidence

ORD record
ord-d0f8e1a2b62f4f1ba2880ebdd75644be
Source dataset
uspto-grants-2001_05
Patent number
US06235747B1

Reaction notes

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