Potassium Iodide → 4'-{3-[(3R)-3-hydroxy-3-methylpyrrolidinyl]propoxy}[1,1'-biphenyl]-4-carbonitrile

HRID 1167846Notes

Reaction equation

HRID 1167846 reaction equation
N[C@@H]1CCN([CH2:7][CH2:8][CH2:9][O:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:22]=[CH:21][C:20]([C:23]#[N:24])=[CH:19][CH:18]=3)=[CH:13][CH:12]=2)C1.[CH3:25][C@@:26]1([OH:31])[CH2:30][CH2:29][NH:28][CH2:27]1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CN(C=O)C>[OH:31][C@:26]1([CH3:25])[CH2:30][CH2:29][N:28]([CH2:7][CH2:8][CH2:9][O:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:22]=[CH:21][C:20]([C:23]#[N:24])=[CH:19][CH:18]=3)=[CH:13][CH:12]=2)[CH2:27]1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 99231474'-{3-[(3R)-3-Aminopyrrolidinyl]propoxy}[1,1'-biphenyl]-4-carbonitrileHCID 55288331(3R)-3-Methylpyrrolidin-3-ol

Product 1

HCID 693556004'-{3-[(3R)-3-hydroxy-3-methylpyrrolidinyl]propoxy}[1,1'-biphenyl]-4-carbonitrileYield 40%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4′-{3-[(3R)-3-Aminopyrrolidinyl]propoxy}[1,1′-biphenyl]-4-carbonitrile (177 mg, 0.65 mmol), (3R)-3-methyl-3-pyrrolidinol (75 mg, 0.74 mmol), potassium carbonate (153 mg) and potassium iodide (184 mg) in 10 mL of DMF were heated at 110° C. for 10 hours. The mixture was evaporated under reduced pressure and the residue was purified by chromatography (CHCl3:MeOH:NH4OH, 9:1:0.1) to provide the title compound (40% yield).

Workup

  1. customThe mixture was evaporated under reduced pressure
  2. customthe residue was purified by chromatography (CHCl3:MeOH:NH4OH, 9:1:0.1)

Sources & evidence

ORD record
ord-841be8ca02c743fc89a4f6cbfe8d3850
Source dataset
uspto-grants-2003_09
Patent number
US06620839B2

Reaction notes

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