Sodium Iodide → HCID 178439092, compound

HRID 1013053Notes

Reaction equation

HRID 1013053 reaction equation
[CH:1]([C:4]1[CH:8]=[C:7]([CH:9]([CH3:11])[CH3:10])[N:6]([C@@H:12]2[CH2:17][CH2:16][C@H:15]([OH:18])[CH2:14][CH2:13]2)[N:5]=1)([CH3:3])[CH3:2].[H-].[Na+].[H][H].Cl[CH2:24][CH2:25][CH2:26][N:27]1[CH2:31][CH2:30][CH2:29][CH2:28]1.[Na+].[I-]>CN(C=O)C>[CH:1]([C:4]1[CH:8]=[C:7]([CH:9]([CH3:11])[CH3:10])[N:6]([C@H:12]2[CH2:13][CH2:14][C@@H:15]([O:18][CH2:24][CH2:25][CH2:26][N:27]3[CH2:31][CH2:30][CH2:29][CH2:28]3)[CH2:16][CH2:17]2)[N:5]=1)([CH3:2])[CH3:3]

Participants

7

Reactant 5

HCID 5238Sodium IodideHCID 24758Sodium hydrideHCID 113210281-(3-Chloropropyl)-pyrrolidineHCID 178418361HCID 178418361, compoundHCID 178439090HCID 178439090, compound

Product 1

HCID 178439092HCID 178439092, compoundYield 43.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Cis-4-(3,5-diisopropyl-pyrazol-1-yl)-cyclohexanol (17.5 mg, 0.068 mmol) was dissolved in dry DMF (2 mL) followed by addition of NaH (excess, 60% in oil) and stirred at room temperature until hydrogen evolution stopped. To the reaction was added 1-(3-Chloro-propyl)-pyrrolidine (20 mg) and catalytic NaI followed by heating to 80° C. overnight. The reaction was cooled, quenched with methanol and concentrated under reduced pressure. The residue was purified by prep HPLC to give the desired product (yield 10.6 mg). LC-MS (C22H39N3O calculated 361) m/z 362 (M+H).

Workup

  1. temperatureThe reaction was cooled
  2. customquenched with methanol
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by prep HPLC

Sources & evidence

ORD record
ord-d3e5c7f2910d456ca5a848eb2829357b
Source dataset
uspto-grants-2011_07
Patent number
US07981896B2

Reaction notes

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