Potassium Carbonate → HCID 53992958, compound

HRID 265919Notes

Reaction equation

HRID 265919 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%

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 (3x) 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 (3x) 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-890164aa1de049b5ac2c77bb3b44dd2a
Source dataset
uspto-grants-1997_07
Patent number
US05648366

Reaction notes

Loading…