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

HRID 1862776ノート

反応式

HRID 1862776 の反応式
[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

参加物

6

反応物 5

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

生成物 1

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

反応条件

温度
100 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-9287e8be4d834ecda1d4444a197b0155
出典データセット
uspto-grants-2003_03
特許番号
US06537994B2

反応ノート

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