Water → HCID 136341325, compound

HRID 1506183Notes

Reaction equation

HRID 1506183 reaction equation
[C:1]([CH2:3]P(=O)(OCC)OCC)#[N:2].[H-].[Na+].[C:14]1([CH:26]2[CH2:31][CH2:30][C:29](=O)[CH2:28][CH2:27]2)[N:15]=[N:16][N:17]2[C:22]=1[C:21]1[CH:23]=[CH:24][NH:25][C:20]=1[N:19]=[CH:18]2.O>O1CCCC1>[C:14]1([CH:26]2[CH2:31][CH2:30][C:29](=[CH:3][C:1]#[N:2])[CH2:28][CH2:27]2)[N:15]=[N:16][N:17]2[C:22]=1[C:21]1[CH:23]=[CH:24][NH:25][C:20]=1[N:19]=[CH:18]2

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 75676Diethyl (cyanomethyl)phosphonateHCID 136341326HCID 136341326, compound

Product 1

HCID 136341325HCID 136341325, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diethyl (cyanomethyl)phosphonate (37.0 μL, 0.235 mmol) in tetrahydrofuran (1 mL) was mixed with sodium hydride (55 wt % dispersion in mineral oil, 10.0 mg, 0.235 mmol) under cooling with ice and then stirred for 30 minutes. The reaction mixture was mixed with 4-(7H-pyrrolo[3,2-e][1,2,3]triazolo[1,5-c]pyrimidin-1-yl)cyclohexanone (20.0 mg, 0.0783 mmol) obtained in Synthetic Examplea 82 and then stirred at room temperature for 30 minutes. After addition of water, the reaction mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/2→1/1→1/0 (v/v)) to give the title compound as a colorless solid (20.0 mg, yield 92%).

Workup

  1. temperatureunder cooling with ice
  2. customobtained in Synthetic Examplea 82
  3. stirringstirred at room temperature for 30 minutes
  4. extractionthe reaction mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with saturated aqueous sodium chloride
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/2→1/1→1/0 (v/v))

Sources & evidence

ORD record
ord-b38eec89313f4a6dae1caa5a0f77b9fc
Source dataset
uspto-grants-2015_12
Patent number
US09216999B2

Reaction notes

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