HCID 86686018, compound → HCID 86686019, compound

HRID 2277724Notes

Reaction equation

HRID 2277724 reaction equation
C([O:3][C:4]([C:6]1([C:19]2[CH:24]=[N:23][CH:22]=[C:21]([Cl:25])[N:20]=2)[CH2:11][CH2:10][CH2:9][N:8]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:7]1)=[O:5])C>C1COCC1.[OH-].[Na+]>[C:15]([O:14][C:12]([N:8]1[CH2:9][CH2:10][CH2:11][C:6]([C:19]2[CH:24]=[N:23][CH:22]=[C:21]([Cl:25])[N:20]=2)([C:4]([OH:5])=[O:3])[CH2:7]1)=[O:13])([CH3:18])([CH3:16])[CH3:17]

Participants

4

Reactant 1

HCID 86686018HCID 86686018, compound

Product 1

HCID 86686019HCID 86686019, compoundYield 38.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of 3-(6-chloro-pyrazin-2-yl)-piperidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-ethyl ester (350.1 mmol) in THF (360 mL) and 1.5 N aqueous NaOH (360 mL) was heated at 80° C. for 5 hr. After it was cooled to room temperature, the aqueous layer was separated and then carefully acidified to pH=5 by the addition of 1 N aqueous HCl solution. The resulting mixture was extracted with DCM (300 mL×3) and the combined organic layers were dried over anhy. Na2SO4, filtered and concentrated under reduced pressure to give a crude tile compound (46 g), which was used directly in the next step without further purification.

Workup

  1. customthe aqueous layer was separated
  2. additioncarefully acidified to pH=5 by the addition of 1 N aqueous HCl solution
  3. extractionThe resulting mixture was extracted with DCM (300 mL×3)
  4. customthe combined organic layers were dried over anhy
  5. filtrationNa2SO4, filtered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-46698c3618f34adbbc0b05e2eae696ff
Source dataset
uspto-grants-2015_09
Patent number
US09133158B2

Reaction notes

Loading…