Sodium Acetate → HCID 54586777, compound

HRID 2093467Notes

Reaction equation

HRID 2093467 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-0b9aa62b7e5b424f8ce342150d34dd81
Source dataset
uspto-grants-2013_05
Patent number
US08445499B2

Reaction notes

Loading…