Potassium Iodide → HCID 58863506, compound

HRID 1667111Notes

Reaction equation

HRID 1667111 reaction equation
[C:1]1([NH2:12])[C:6](F)=[C:5](F)C(F)=C(N)C=1F.Cl.Cl.Br[CH:16]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[C:29](=O)([O-])[O-].[K+].[K+].[I-].[K+].C[N:38]([CH3:41])C=O>>[CH:16]([N:12]1[CH2:29][CH2:41][NH:38][C@H:6]([CH3:5])[CH2:1]1)([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 5

HCID 4875Potassium IodideHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 149026Tetrafluoro-m-phenylenediamine dihydrochlorideHCID 236603Bromodiphenylmethane

Product 1

HCID 58863506HCID 58863506, compound

Procedure

A solution of the dihydrochloride of R-methylpiperazine (Tetrahedron Lett. 1994, 35, 16, 2533-2536)(0.42 g, 2.42 mmol) in N,N-dimethylformamide (3 mL) was treated with bromodiphenylmethane (0.6 g, 2.42 mmol), potassium carbonate (1.17 g, 8.5 mmol), and a catalytic amount of potassium iodide. The resultant reaction mixture was then stirred at ambient temperature overnight. Then the reaction mixture was concentrated and partitioned between water/methylene chloride. The organic layer was dried over magnesium sulfate, concentrated and the residue was purified by preparative HPLC on a Waters Nova-Pak® HR C18 6 um 60 Å Prep-Pak® cartridge column (40 mm×100 mm) using a gradient of 10% to 100% acetonitrile in 10 mM aqueous ammonium acetate over 12 minutes at a flow rate of 70 mL/min to provide the title compound.

Workup

  1. customThe resultant reaction mixture
  2. concentrationThen the reaction mixture was concentrated
  3. custompartitioned between water/methylene chloride
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. concentrationconcentrated
  6. customthe residue was purified by preparative HPLC on a Waters Nova-Pak® HR
  7. customover 12 minutes

Sources & evidence

ORD record
ord-16323223e2ae4bc0bab0280e745dcb1b
Source dataset
uspto-grants-2011_10
Patent number
US08044069B2

Reaction notes

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