Pyridine → 4-[(2S)-3-(2-{4-[2-(2-Cyclopentyl-ethyl)-imidazo[4,5-b]pyridin-3-yl]-phenyl}-ethylamino)-2-hydroxy-propoxy]-phenol

HRID 1862776Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1862776
[NH2:1][C:2]1[C:3]([NH:8][C:9]2[CH:24]=[CH:23][C:12]([CH2:13][CH2:14][NH:15][C:16](=O)OC(C)(C)C)=[CH:11][CH:10]=2)=[N:4][CH:5]=[CH:6][CH:7]=1.[CH:25]1([CH2:30][CH2:31][C:32](Cl)=[O:33])[CH2:29][CH2:28]CC1.C(Cl)(Cl)Cl.C[OH:40].C([O:44][CH2:45][CH3:46])(=O)C.[CH3:47][CH2:48][CH2:49]CCC.N1[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1>>[CH:54]1([CH2:47][CH2:48][C:49]2[N:8]([C:9]3[CH:10]=[CH:11][C:12]([CH2:13][CH2:14][NH:15][CH2:16][C@H:45]([OH:44])[CH2:46][O:40][C:25]4[CH:29]=[CH:28][C:32]([OH:33])=[CH:31][CH:30]=4)=[CH:23][CH:24]=3)[C:3]3=[N:4][CH:5]=[CH:6][CH:7]=[C:2]3[N:1]=2)[CH2:58][CH2:57][CH2:56][CH2:55]1

Komponenten

6

Edukt 5

HCID 1049PyridineHCID 660393-Cyclopentylpropionyl chlorideHCID 18619625Tert-butyl 4-[(3-amino-2-pyridinyl)amino]phenethylcarbamateHCID 21226206Ethyl acetate hexaneHCID 21584188Chloroform methanol

Produkt 1

HCID 700065644-[(2S)-3-(2-{4-[2-(2-Cyclopentyl-ethyl)-imidazo[4,5-b]pyridin-3-yl]-phenyl}-ethylamino)-2-hydroxy-propoxy]-phenol

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

tert-Butyl 4-[(3-amino-2-pyridinyl)amino]phenethylcarbamate (1.0 g, 3.05 mmol) was dissolved in anhydrous pyridine and 3-cyclopentylpropanoyl chloride (0.489 g, 3.04 mmol) added. The reaction was heated at 100° C. for 18 hours. The solvent was removed and the residue partitioned between water and chloroform. The organic phase was washed with water and brine, dried over anhydrous magnesium sulfate and filtered. The solution was taken to dryness in vacuo and the residue purified by flash chromatography on silica gel Merck-60 (eluant 20:1 chloroform-methanol followed by 1:1 ethyl acetate-hexane) to yield the title compound (0.93 g, 2.14 mmol).

Aufarbeitung

  1. customThe solvent was removed
  2. customthe residue partitioned between water and chloroform
  3. washThe organic phase was washed with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customthe residue purified by flash chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-9287e8be4d834ecda1d4444a197b0155
Quelldatensatz
uspto-grants-2003_03
Patentnummer
US06537994B2

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