Triethylamine → HCID 22351258, compound

HRID 993130Notes

Reaction equation

HRID 993130 reaction equation
[Cl:1][CH2:2][CH:3]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[O:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]([NH:23][C:24]2[CH:29]=[CH:28][C:27]([C:30]#[N:31])=[CH:26][CH:25]=2)[CH2:12][NH:13][S:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)(=[O:16])=[O:15])=[CH:7][C:6]=1[O:32][CH3:33].Cl.NO.C([N:45](CC)CC)C.C(=O)([O-])[O-].[K+].[K+]>C(O)C>[C:17]1([S:14]([NH:13][CH2:12][CH:11]([NH:23][C:24]2[CH:25]=[CH:26][C:27]([C:30]([NH2:45])=[NH:31])=[CH:28][CH:29]=2)[C:8]2[CH:9]=[CH:10][C:5]([O:4][CH:3]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[CH2:2][Cl:1])=[C:6]([O:32][CH3:33])[CH:7]=2)(=[O:15])=[O:16])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 22351315HCID 22351315, compound

Product 1

HCID 22351258HCID 22351258, compoundYield 30.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

N-[2-[4-(2-chloro-1-phenyl-ethoxy)-3-methoxy-phenyl]-2-(4-cyano-phenylamino)-ethyl]-benzenesulfonamide (100 mg 0.18 mmoles) was dissolved in ethanol (3 ml) and hydroxylaminehydrochloride (62 mg, 0.89 mmoles) added. To this was added triethylamine (90 mg, 0.89 mmoles) and later potassium carbonate (62 mg). The reaction was heated to 80° C. for 48 hours. The reaction was cooled and the solvent removed in vacuo. The residue was taken up in ethyl acetate and washed twice with water and once with brine. The solution was dried over sodium sulfate and the solvent removed. The crude intermediate was dissolved in methanol (4 ml) and a few drops of acetic acid added. Approximately 50-100 mg of Raney nickel suspended in sodium hydroxide (Aldrich) was added and the reaction placed under an atmosphere of hydrogen. The suspension was stirred vigorously for 8 hours, the catalyst filtered off and the solvent removed in vacuo. The crude product was purified by reverse-phase chromatography to yield 4-{2-benzenesulfonylamino-1-[4-(2-chloro-1-phenyl-ethoxy)-3-methoxy-phenyl]-ethylamino}-benzamidine (32 mg). MS(M+H)=579.

Workup

  1. temperatureThe reaction was cooled
  2. customthe solvent removed in vacuo
  3. washwashed twice with water and once with brine
  4. dry with materialThe solution was dried over sodium sulfate
  5. customthe solvent removed
  6. dissolutionThe crude intermediate was dissolved in methanol (4 ml)
  7. additiona few drops of acetic acid added
  8. additionwas added
  9. filtrationthe catalyst filtered off
  10. customthe solvent removed in vacuo
  11. customThe crude product was purified by reverse-phase chromatography

Sources & evidence

ORD record
ord-8fb1936406e84aefb91d7ba60b475a5f
Source dataset
uspto-grants-2002_10
Patent number
US06472393B1

Reaction notes

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