Cesium carbonate → HCID 58355485, compound

HRID 1184106Notes

Reaction equation

HRID 1184106 reaction equation
[Cl:1][C:2]1[C:10]2[N:9]=[C:8]([C:11]([N:13]([CH2:31][CH:32]([CH3:34])[CH3:33])[C@@H:14]3[CH2:19][N:18]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:17][C@H:16]([C:27]([O:29][CH3:30])=[O:28])[CH2:15]3)=[O:12])[NH:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.CS(O[CH2:40][CH2:41][CH2:42][CH2:43][O:44][CH3:45])(=O)=O.C(=O)([O-])[O-].[Cs+].[Cs+]>CC(N(C)C)=O>[Cl:1][C:2]1[C:10]2[N:9]([CH2:40][CH2:41][CH2:42][CH2:43][O:44][CH3:45])[C:8]([C:11]([N:13]([CH2:31][CH:32]([CH3:34])[CH3:33])[C@@H:14]3[CH2:19][N:18]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:17][C@H:16]([C:27]([O:29][CH3:30])=[O:28])[CH2:15]3)=[O:12])=[N:7][C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 116870064-Methoxybutyl methanesulfonateHCID 58355645HCID 58355645, compound

Product 1

HCID 58355485HCID 58355485, compoundYield 10%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
70 °C

Procedure

1-tert-Butyl 3-methyl (3R,5S)-5-{[(4-chloro-1H-benzimidazol-2-yl)carbonyl](2-methylpropyl)amino}piperidine-1,3-dicarboxylate (1.7 g) and 4-methoxybutyl methanesulfonate (754 mg) were dissolved in DMA (50 ml), cesium carbonate (1.7 g) was added, and the mixture was stirred at 70° C. for 12 hr. The reaction mixture was poured into ice water (100 ml), and the mixture was extracted twice with ethyl acetate (100 ml). The extract was washed with brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was subjected to silica gel column chromatography, and a less polar fraction eluted with ethyl acetate-hexane (1:4-1:1) was concentrated under reduced is pressure to give 1-tert-butyl 3-methyl (3R,5S)-5-[{[7-chloro-1-(4-methoxybutyl)-1H-benzimidazol-2-yl]carbonyl}(2-methylpropyl)amino]piperidine-1,3-dicarboxylate (200 mg).

Workup

  1. extractionthe mixture was extracted twice with ethyl acetate (100 ml)
  2. washThe extract was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. washa less polar fraction eluted with ethyl acetate-hexane (1:4-1:1)
  6. concentrationwas concentrated

Sources & evidence

ORD record
ord-92028428aea14f4b80f6490392abd4da
Source dataset
uspto-grants-2014_03
Patent number
US08664380B2

Reaction notes

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