Potassium Carbonate → HCID 53992958, compound

HRID 343653Notes

Reaction equation

HRID 343653 reaction equation
CS(O[CH2:6][CH2:7][C:8]1([C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[C:27]([Cl:32])[CH:26]=2)[CH2:12][CH2:11][N:10]([C:13](=[O:24])[C:14]2[C:19]([O:20][CH3:21])=[CH:18][CH:17]=[CH:16][C:15]=2[O:22][CH3:23])[CH2:9]1)(=O)=O.[C:33]1([N:39]2[C:43]3([CH2:48][CH2:47][NH:46][CH2:45][CH2:44]3)[C:42](=[O:49])[NH:41][CH2:40]2)[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.C(=O)([O-])[O-].[K+].[K+]>C1COCC1.O>[Cl:32][C:27]1[CH:26]=[C:25]([C:8]2([CH2:7][CH2:6][N:46]3[CH2:45][CH2:44][C:43]4([N:39]([C:33]5[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=5)[CH2:40][NH:41][C:42]4=[O:49])[CH2:48][CH2:47]3)[CH2:12][CH2:11][N:10]([C:13](=[O:24])[C:14]3[C:15]([O:22][CH3:23])=[CH:16][CH:17]=[CH:18][C:19]=3[O:20][CH3:21])[CH2:9]2)[CH:30]=[CH:29][C:28]=1[Cl:31]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 705561-Phenyl-1,3,8-triazaspiro(4.5)decan-4-oneHCID 53797274HCID 53797274, compound

Product 1

HCID 53992958HCID 53992958, compoundYield 51.2%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

2-[1-(2,6-Dimethoxy-benzoyl)-3-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]-ethyl methanesulfonate (200 mg, 0.398 mmol), and 1-phenyl-1,3,8-triaza-spiro[4.5]decan-4-one (100 mg, 0.432 mmol) were dissolved in THF/H2O (4 mL /1 mL) and treated with potassium carbonate (110 mg, 0.796 mmol, 2 eq.) at reflux for 22 hours. The solution was concentrated in vacuo and the aqueous phase was extracted (3×) with dichloromethane. The organic phase was dried over magnesium sulfate, filtered, and concentrated in vacuo. The residue was chromatographed on silica gel (40 g) with a gradient from ethyl acetate to 10% methanol in dichloromethane to give 130 mg (51%) of the title compound.

Workup

  1. temperatureat reflux for 22 hours
  2. concentrationThe solution was concentrated in vacuo
  3. extractionthe aqueous phase was extracted (3×) with dichloromethane
  4. dry with materialThe organic phase was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was chromatographed on silica gel (40 g) with a gradient from ethyl acetate to 10% methanol in dichloromethane

Sources & evidence

ORD record
ord-18b6be607125418db50aa301ff7c9d47
Source dataset
uspto-grants-1999_01
Patent number
US05861416

Reaction notes

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