Potassium Carbonate → HCID 57566162, compound

HRID 1728100Notes

Reaction equation

HRID 1728100 reaction equation
C(OC([N:8]1[C:38]2[C:33](=[CH:34][CH:35]=[C:36]([Cl:39])[CH:37]=2)[C:10]2([CH:15]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[CH:17]=3)[CH2:14][C:13](=[O:23])[NH:12][CH:11]2[C:24]2[CH:29]=[C:28]([F:30])[CH:27]=[CH:26][C:25]=2[CH2:31]Br)[C:9]1=[O:40])=O)(C)(C)C.C([O-])([O-])=O.[K+].[K+].[CH3:47][S:48]([N:51]1[CH2:56][CH2:55][NH:54][CH2:53][CH2:52]1)(=[O:50])=[O:49]>C(#N)C>[Cl:39][C:36]1[CH:37]=[C:38]2[NH:8][C:9](=[O:40])[C@:10]3([C@H:15]([C:16]4[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[CH:17]=4)[CH2:14][C:13](=[O:23])[NH:12][C@@H:11]3[C:24]3[CH:29]=[C:28]([F:30])[CH:27]=[CH:26][C:25]=3[CH2:31][N:54]3[CH2:55][CH2:56][N:51]([S:48]([CH3:47])(=[O:50])=[O:49])[CH2:52][CH2:53]3)[C:33]2=[CH:34][CH:35]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 7091611-(Methylsulfonyl)piperazineHCID 76567951HCID 76567951, compound

Product 1

HCID 57566162HCID 57566162, compoundYield 17.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of racemic (2′R,3R,4′S)-2′-(2-bromomethyl-5-fluoro-phenyl)-6-chloro-4′-(3-chlorophenyl)-2,3-dihydro-2,6′-dioxo-spiro[indole-3,3′-piperidine]-1-carboxylic acid tert-butyl ester (30 mg, 0.046 mmol) prepared in example 164b in acetonitrile (5 mL) was added K2CO3 (13 mg, 0.094 mmol) and 1-methanesulfonyl-piperazine (15 mg, 0.094 mmol). The mixture was refluxed for 2 h, concentrated. The residue was dissolved in trifluoroacetic acid and stirred at room temperature for 30 min, then concentrated and purified by prep-HPLC to give (2′R,3R,4′S)-6-chloro-4′-(3-chlorophenyl)-2′-[5-fluoro-2-(4-methanesulfonyl-piperazin-1-yl)methyl-phenyl]-spiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione as solid (5 mg, 17%).

Workup

  1. temperatureThe mixture was refluxed for 2 h
  2. concentrationconcentrated
  3. dissolutionThe residue was dissolved in trifluoroacetic acid
  4. concentrationconcentrated
  5. custompurified by prep-HPLC

Sources & evidence

ORD record
ord-ab78f1745afa4ddbac83c75fbdb18692
Source dataset
uspto-grants-2009_02
Patent number
US07495007B2

Reaction notes

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