Tetrahydrofuran → (5-((6-(1-Acetylpyrrolidin-2-yl)-2-pyridin-2-yl-1H-benzimidazol-5-yl)oxy)pyridin-2-yl)methanol

HRID 13403Notes

Reaction equation

HRID 13403 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].O1CCCC1.[C:12]([N:15]1[CH2:19][CH2:18][CH2:17][CH:16]1[C:20]1[C:21]([O:35][C:36]2[CH:37]=[CH:38][C:39]([C:42](OCC)=[O:43])=[N:40][CH:41]=2)=[CH:22][C:23]2[N:27]=[C:26]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=3)[NH:25][C:24]=2[CH:34]=1)(=[O:14])[CH3:13]>C(Cl)(Cl)Cl>[C:12]([N:15]1[CH2:19][CH2:18][CH2:17][CH:16]1[C:20]1[C:21]([O:35][C:36]2[CH:37]=[CH:38][C:39]([CH2:42][OH:43])=[N:40][CH:41]=2)=[CH:22][C:23]2[N:27]=[C:26]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=3)[NH:25][C:24]=2[CH:34]=1)(=[O:14])[CH3:13]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 21226445Aluminium lithium hydrideHCID 23145214Ethyl 5-((6-(1-Acetylpyrrolidin-2-yl)-2-pyridin-2-yl-1H-benzimidazol-5-yl)oxy)pyridine-2-carboxylate

Product 1

HCID 23145233(5-((6-(1-Acetylpyrrolidin-2-yl)-2-pyridin-2-yl-1H-benzimidazol-5-yl)oxy)pyridin-2-yl)methanol

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

20 mg of lithiumaluminium hydride was added to a tetrahydrofuran (2 ml) solution of 90 mg of ethyl 5-((6-(1-acetylpyrrolidin-2-yl)-2-pyridin-2-yl-1H-benzimidazol-5-yl)oxy)pyridine-2-carboxylate obtained in Example 495 with cooling with ice, and the reaction liquid was stirred at 0° C. for 30 minutes. The reaction liquid was diluted with chloroform, washed with aqueous saturated ammonium chloride, aqueous saturated sodium bicarbonate and saturated saline in order, and dried with anhydrous sodium 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), chloroform/methanol=10/1) to obtain the entitled compound as a white solid.

Workup

  1. temperaturewith cooling with ice
  2. customthe reaction liquid
  3. customThe reaction liquid
  4. washwashed with aqueous saturated ammonium chloride, aqueous saturated sodium bicarbonate and saturated saline in order
  5. dry with materialdried with anhydrous sodium 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), chloroform/methanol=10/1)

Sources & evidence

ORD record
ord-72b26696627843209e97b1f706cf6601
Source dataset
uspto-grants-2010_06
Patent number
US07728025B2

Reaction notes

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