2-Phenylethanol → 1-(2-(6-phenethyloxy-2-pyridin-2-yl-3-(2-trimethylsilanyl-ethoxymethyl)-3H-benzimidazol-5-yl)-pyrrolidin-1-yl)-ethanone

HRID 13273

반응식

HRID 13273 반응식
C(NC(C)C)(C)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:27]1([CH2:33][CH2:34][OH:35])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.O[C:37]1[C:38]([CH:60]2[CH2:64][CH2:63][CH2:62][N:61]2[C:65](=[O:67])[CH3:66])=[CH:39][C:40]2[N:44]([CH2:45][O:46][CH2:47][CH2:48][Si:49]([CH3:52])([CH3:51])[CH3:50])[C:43]([C:53]3[CH:58]=[CH:57][CH:56]=[CH:55][N:54]=3)=[N:42][C:41]=2[CH:59]=1.C(=O)(O)[O-].[Na+]>O1CCCC1>[CH2:34]([O:35][C:37]1[C:38]([CH:60]2[CH2:64][CH2:63][CH2:62][N:61]2[C:65](=[O:67])[CH3:66])=[CH:39][C:40]2[N:44]([CH2:45][O:46][CH2:47][CH2:48][Si:49]([CH3:52])([CH3:51])[CH3:50])[C:43]([C:53]3[CH:58]=[CH:57][CH:56]=[CH:55][N:54]=3)=[N:42][C:41]=2[CH:59]=1)[CH2:33][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

참가 물질

7

반응물 5

HCID 60542-Phenylethanol2회HCID 7912Diisopropylamine2회HCID 11776Triphenylphosphine2회HCID 516892Sodium BicarbonateHCID 231452771-(2-(6-hydroxy-2-pyridin-2-yl-3-(2-trimethylsilanyl-ethoxymethyl)-3H-benzimidazol-5-yl)-pyrrolidin-1-yl)-ethanone

생성물 1

HCID 231455911-(2-(6-phenethyloxy-2-pyridin-2-yl-3-(2-trimethylsilanyl-ethoxymethyl)-3H-benzimidazol-5-yl)-pyrrolidin-1-yl)-ethanone

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

0.019 ml of diisopropylamine, 27.6 mg of triphenyl phosphine and 0.011 ml of 2-phenyl-ethanol were added in order to a tetrahydrofuran (1 ml) solution of 29.2 mg of 1-(2-(6-hydroxy-2-pyridin-2-yl-3-(2-trimethylsilanyl-ethoxymethyl)-3H-benzimidazol-5-yl)pyrrolidin-1-yl)-ethanone obtained in Example 121 (step 10), and the reaction liquid was stirred for 6 hours at room temperature. 0.040 ml of diisopropylamine, 53.2 mg of triphenyl phosphine and 0.023 ml of 2-phenyl-ethanol were added in order to the reaction liquid, and the reaction liquid was stirred overnight at room temperature. Aqueous saturated sodium bicarbonate was added to the reaction liquid, and this was extracted with ethyl acetate, and dried with anhydrous magnesium sulfate. The solvent was evaporated away under reduced pressure, and the resulting residue was purified through partitioning thin-layer chromatography (Kieselgel™ 60F254, Art 5744 (by Merck), ethyl acetate) to obtain the entitled compound as a brown oily substance.

후처리

  1. customthe reaction liquid
  2. customthe reaction liquid
  3. stirringwas stirred overnight at room temperature
  4. extractionthis was extracted with ethyl acetate
  5. dry with materialdried with anhydrous magnesium sulfate
  6. customThe solvent was evaporated away under reduced pressure
  7. customthe resulting residue was purified
  8. customthrough partitioning thin-layer chromatography (Kieselgel™ 60F254, Art 5744 (by Merck), ethyl acetate)
  9. customto obtain the entitled compound as a brown oily substance

출처 및 근거

ORD 기록
ord-50ff626390254e4b8c9004508484924c
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07728025B2

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