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

HRID 1862776Notes

Reaction equation

HRID 1862776 reaction equation
[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

Participants

6

Reactant 5

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

Product 1

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

Conditions

Temperature
100 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-9287e8be4d834ecda1d4444a197b0155
Source dataset
uspto-grants-2003_03
Patent number
US06537994B2

Reaction notes

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