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

HRID 1862776노트

반응식

HRID 1862776 반응식
[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

참가 물질

6

반응물 5

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

생성물 1

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

반응 조건

온도
100 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-9287e8be4d834ecda1d4444a197b0155
출처 데이터셋
uspto-grants-2003_03
특허 번호
US06537994B2

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