Cesium carbonate → 1-(3-Methylpyrazin-2-yl)-1'-[4-(methylsulfonyl)phenyl]-4,4'-bipiperidine

HRID 2093482Notes

Reaction equation

HRID 2093482 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:16][CH2:15][CH:14]([CH:17]3[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]3)[CH2:13][CH2:12]2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].C(=O)([O-])[O-].[Cs+].[Cs+].Cl[C:30]1[C:35]([CH3:36])=[N:34][CH:33]=[CH:32][N:31]=1>CN1C(=O)CCC1.C(=O)(O)[O-].[Na+]>[CH3:36][C:35]1[C:30]([N:20]2[CH2:21][CH2:22][CH:17]([CH:14]3[CH2:15][CH2:16][N:11]([C:8]4[CH:9]=[CH:10][C:5]([S:2]([CH3:1])(=[O:3])=[O:4])=[CH:6][CH:7]=4)[CH2:12][CH2:13]3)[CH2:18][CH2:19]2)=[N:31][CH:32]=[CH:33][N:34]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 66769Pyrazine, 2-chloro-3-methyl-HCID 59178867HCID 59178867, compound

Product 1

HCID 591789451-(3-Methylpyrazin-2-yl)-1'-[4-(methylsulfonyl)phenyl]-4,4'-bipiperidine

Reagents, catalysts & solvents 2

HCID 13387N-methyl-2-pyrrolidoneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

The 1-[4-(methylsulfonyl)phenyl]-4,4′-bipiperidine (80 mg, 0.25 mmol, prepared as for Example 1, Step 2) and cesium carbonate (243 mg, 0.75 mmol) were slurried in NMP (0.5 ml) and the 2-chloro-3-methylpyrazine (38 mg, 0.30 mmol) added. The mixture was stirred at 150 C overnight. The slurry was diluted with 15% saturated sodium bicarbonate:water (40 ml) and extracted with DCM (3×25 ml). The combined organic fraction was washed with 4:1 water:saturated sodium bicarbonate (2×), brine, dried over magnesium sulfate, filtered, and the volatiles removed in vac. The crude material was purified by chromatography on silica gel with 5% acetone:DCM to yield the titled compound.

Workup

  1. extractionwater (40 ml) and extracted with DCM (3×25 ml)
  2. washThe combined organic fraction was washed with 4:1 water
  3. dry with materialsaturated sodium bicarbonate (2×), brine, dried over magnesium sulfate
  4. filtrationfiltered
  5. customthe volatiles removed in vac
  6. customThe crude material was purified by chromatography on silica gel with 5% acetone

Sources & evidence

ORD record
ord-c7ca952ef9d844cf8b3286a2a5d63a5d
Source dataset
uspto-grants-2013_05
Patent number
US08445499B2

Reaction notes

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