Water → HCID 136341333, compound

HRID 1506189Notes

Reaction equation

HRID 1506189 reaction equation
[I-].[CH3:2][S+](C)C.[H-].[Na+].[C:8]1([CH:20]2[CH2:25][CH2:24][C:23](=[CH:26][C:27]#[N:28])[CH2:22][CH2:21]2)[N:9]=[N:10][N:11]2[C:16]=1[C:15]1[CH:17]=[CH:18][NH:19][C:14]=1[N:13]=[CH:12]2.O>CS(C)=O>[C:8]1([CH:20]2[CH2:21][CH2:22][C:23]3([CH:26]([C:27]#[N:28])[CH2:2]3)[CH2:24][CH2:25]2)[N:9]=[N:10][N:11]2[C:16]=1[C:15]1[CH:17]=[CH:18][NH:19][C:14]=1[N:13]=[CH:12]2

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 75127Trimethylsulfonium iodideHCID 136341325HCID 136341325, compound

Product 1

HCID 136341333HCID 136341333, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Trimethylsulfonium iodide (59.0 μL, 0.269 mmol) in dimethyl sulfoxide (1 mL) was stirred with sodium hydride (55 wt % dispersion in mineral oil, 12.0 mg, 0.269 mmol) at room temperature for 30 minutes. The reaction mixture was mixed with 2-[4-(7H-pyrrolo[3,2-e][1,2,3]triazolo[1,5-c]pyrimidin-1-yl)cyclohexylidene]acetonitrile (15.0 mg, 0.0539 mmol) obtained in Synthetic Examplea 434 and then stirred at room temperature for 15 hours. 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=1/1 (v/v)) to give the title compound as a colorless solid (5.80 mg, yield 37%).

Workup

  1. customobtained in Synthetic Examplea 434
  2. extractionthe reaction mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/1 (v/v))

Sources & evidence

ORD record
ord-d24e6c8f6aa0456697ae150e66a0afe9
Source dataset
uspto-grants-2015_12
Patent number
US09216999B2

Reaction notes

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