Sodium Acetate → HCID 54586777, compound

HRID 1947666Notes

Reaction equation

HRID 1947666 reaction equation
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([N:8]2[CH2:13][CH2:12][CH:11]([CH:14]3[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]3)[CH2:10][CH2:9]2)[CH:3]=1.C([O-])(=O)C.[Na+]>CO.[Pd].O>[N:7]1[CH:2]=[CH:3][C:4]([N:8]2[CH2:13][CH2:12][CH:11]([CH:14]3[CH2:15][CH2:16][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:18][CH2:19]3)[CH2:10][CH2:9]2)=[N:5][CH:6]=1

Participants

6

Reactant 2

HCID 517045Sodium AcetateHCID 59178818HCID 59178818, compound

Product 1

HCID 54586777HCID 54586777, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

The tert-butyl 1′-(6-chloropyrimidin-4-yl)-4,4′-bipiperidine-1-carboxylate (50 mg, 0.13 mmol, prepared as described for Example 13) and sodium acetate (11 mg, 0.13 mmol) were dissolved in methanol (1.3 ml), 10% palladium on carbon (14 mg) added and the solution stirred overnight under a hydrogen atmosphere. The solution was diluted with 4:1 water:saturated sodium bicarbonate (40 ml) and extracted with ethyl acetate (3×25 ml). The combined organic fraction was washed with brine, dried over magnesium sulfate, filtered, and the volatiles removed in vac. The crude material was purified by chromatography on silica gel with 35% acetone:hexanes to yield the titled compound.

Workup

  1. extractionsaturated sodium bicarbonate (40 ml) and extracted with ethyl acetate (3×25 ml)
  2. washThe combined organic fraction was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customthe volatiles removed in vac
  6. customThe crude material was purified by chromatography on silica gel with 35% acetone

Sources & evidence

ORD record
ord-2f05fd4bf95d47259d9fbdf6afa14190
Source dataset
uspto-grants-2013_03
Patent number
US08399485B2

Reaction notes

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