Potassium Iodide → HCID 86588506, compound

HRID 584178Notes

Reaction equation

HRID 584178 reaction equation
[F:1][C:2]([F:37])([F:36])[C:3]1[CH:4]=[C:5]([CH:29]=[C:30]([C:32]([F:35])([F:34])[F:33])[CH:31]=1)[C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]#[C:16][CH2:17][Cl:18])[CH2:10][C@H:9]1[CH2:19][C:20]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[NH:22][CH:21]=1)=[O:7].[CH3:38][O:39][CH2:40][C@H:41]1[CH2:45][CH2:44][CH2:43][NH:42]1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CN(C)C=O.O>[ClH:18].[ClH:18].[F:1][C:2]([F:37])([F:36])[C:3]1[CH:4]=[C:5]([CH:29]=[C:30]([C:32]([F:35])([F:34])[F:33])[CH:31]=1)[C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]#[C:16][CH2:17][N:42]2[CH2:43][CH2:44][CH2:45][C@@H:41]2[CH2:40][O:39][CH3:38])[CH2:10][C@H:9]1[CH2:19][C:20]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[NH:22][CH:21]=1)=[O:7]

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 671216(2R)-2-(Methoxymethyl)pyrrolidineHCID 53993986HCID 53993986, compound

Product 1

HCID 86588506HCID 86588506, compoundYield 118.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of (2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-[(1H-indol-3-yl)methyl]-4-(4-chloro-2-butynyl)piperazine (0.25 g), (R)-2-(methoxymethyl)pyrrolidine (0.10 g), potassium carbonate (0.25 g) and potassium iodide (10 mg) in dry N,N-dimethylformamide (5 ml) was stirred for 5 hours at room temperature. The mixture was poured into water and extracted with ethyl acetate. The extract was washed with brine, dried over magnesium sulfate and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel using ethyl acetate as eluent and treated with 4N hydrogen chloride in ethyl acetate solution to give (2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-[(1H-indol-3-yl)methyl]-4-[4-[(2R)-2-(methoxymethyl)pyrrolidino]-2-butynyl]piperazine dihydrochloride (0.19 g).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel
  6. additiontreated with 4N hydrogen chloride in ethyl acetate solution

Sources & evidence

ORD record
ord-1d1f96c494964b9a9dd2c992a41885e2
Source dataset
uspto-grants-2005_08
Patent number
US06924278B2

Reaction notes

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