Tetrahydrofuran → HCID 178438698, compound

HRID 1412361Notes

Reaction equation

HRID 1412361 reaction equation
C([O:3][C:4](=O)[CH2:5][O:6][C@H:7]1[CH2:10][C@H:9]([N:11]2[C:16](=[O:17])[C:15]([CH2:18][C:19]3[CH:24]=[CH:23][C:22]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=4[C:31]#[N:32])=[CH:21][CH:20]=3)=[C:14]([CH2:33][CH2:34][CH3:35])[N:13]3[N:36]=[CH:37][N:38]=[C:12]23)[CH2:8]1)C.[CH2:40]([Mg]Br)[CH3:41].[Cl-].[NH4+].O1CC[CH2:48][CH2:47]1>>[CH2:47]([C:4]([OH:3])([CH2:40][CH3:41])[CH2:5][O:6][C@H:7]1[CH2:8][C@H:9]([N:11]2[C:16](=[O:17])[C:15]([CH2:18][C:19]3[CH:24]=[CH:23][C:22]([C:25]4[C:26]([C:31]#[N:32])=[CH:27][CH:28]=[CH:29][CH:30]=4)=[CH:21][CH:20]=3)=[C:14]([CH2:33][CH2:34][CH3:35])[N:13]3[N:36]=[CH:37][N:38]=[C:12]23)[CH2:10]1)[CH3:48]

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 178418443HCID 178418443, compoundHCID 178438700HCID 178438700, compound

Product 1

HCID 178438698HCID 178438698, compoundYield 76%

Procedure

Ethyl[(trans-3-{6-[(2′-cyanobiphenyl-4-yl)methyl]-5-oxo-7-propyl[1,2,4]triazolo[1,5-a]pyrimidin-4(5H)-yl}cyclobutyl)oxy]acetate (0.077 g) was dissolved in tetrahydrofuran (10 mL), and ethylmagnesium bromide (3.0 M diethyl ether solution, 0.15 mL) was added at room temperature. The reaction mixture was stirred for 6 hr, saturated aqueous ammonium chloride solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The obtained ethyl acetate layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to give the title compound as a colorless solid (0.06 g, 76%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe obtained ethyl acetate layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-dfcb03c4c293495bb8b3eaa0ef141155
Source dataset
uspto-grants-2014_12
Patent number
US08921379B2

Reaction notes

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