Dimethylformamide → HCID 117987851, compound

HRID 2206223Notes

Reaction equation

HRID 2206223 reaction equation
[CH:1]1([N:6]2[C:14]3[CH:13]=[CH:12][N:11]=[C:10]([O:15][CH3:16])[C:9]=3[C:8]([C:17]3[CH:18]=[C:19](C(N)=O)[S:20][CH:21]=3)=[N:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].IC.[Cl-].[NH4+].[CH3:31][N:32]([CH:34]=[O:35])[CH3:33]>>[CH:1]1([N:6]2[C:14]3[CH:13]=[CH:12][N:11]=[C:10]([O:15][CH3:16])[C:9]=3[C:8]([C:17]3[CH:18]=[C:19]([C:34]([N:32]([CH3:33])[CH3:31])=[O:35])[S:20][CH:21]=3)=[N:7]2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 117987637HCID 117987637, compound

Product 1

HCID 117987851HCID 117987851, compound

Procedure

4-(1-Cyclopentyl-4-methoxy-1H-pyrazolo[4,3-c]pyridin-3-yl)thiophene-2-carboxamide (51.0 mg) was added to a solution of sodium hydride (60% dispersion in mineral oil, 30.0 mg) in DMF (10 ml), and the mixture was stirred at room temperature for 30 min. To the reaction mixture was added iodomethane (0.023 mL), and the mixture was stirred overnight at room temperature. To the reaction mixture was added saturated aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate. The organic layer was washed successively with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (55.0 mg).

Workup

  1. stirringthe mixture was stirred overnight at room temperature
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed successively with water and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-ac775a3ff5e24b629976290078cba2a1
Source dataset
uspto-grants-2016_06
Patent number
US09371320B2

Reaction notes

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