Dimethylformamide → HCID 178518224, compound

HRID 855856Notes

Reaction equation

HRID 855856 reaction equation
[NH2:1][C@H]1CC[C@H](O)CC1.[H-].[Na+].[Cl:11][C:12]1C=C[C:15]([C:18]#[N:19])=[CH:14][N:13]=1.[CH3:20][N:21]([CH:23]=[O:24])C>C(OCC)(=O)C>[CH:14]1[N:13]=[C:12]([Cl:11])[N:19]=[C:18]2[C:23]([N:21]=[CH:20][NH:1][C:15]=12)=[O:24]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 51520946-Chloro-3-pyridinecarbonitrileHCID 178511715HCID 178511715, compound

Product 1

HCID 178518224HCID 178518224, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of trans-4-aminocyclohexanol (115 mg, 1 mmol) in DMF (6 mL) at 0° C. was added 60% NaH in mineral oil (120 mg, 3 mmol). The reaction mixture was stirred at 0° C. for ½ hour and then 2-chloro-5-cyanopyridine (151 mg, 1.25 mmol) was added. It was heated to 60° C. for 2 hours and stirred for 12 hours at room temperature. The reaction mixture was diluted with ethyl acetate and washed with water (3 times) and brine. The organic layer was dried (sodium sulfate), filtered, and concentrated under reduced pressure to provide the titled compound. MS (DCI) m/z 218 (M+H)+.

Workup

  1. temperatureIt was heated to 60° C. for 2 hours
  2. stirringstirred for 12 hours at room temperature
  3. washwashed with water (3 times) and brine
  4. dry with materialThe organic layer was dried (sodium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c5104ef2c18a479295d3a980cdd32b66
Source dataset
uspto-grants-2007_08
Patent number
US07262207B2

Reaction notes

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