HCID 10269934, compound → HCID 23577286, compound

HRID 1827215Notes

Reaction equation

HRID 1827215 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([CH2:17][NH:18][C:19]2[C:24](Cl)=[N:23][CH:22]=[CH:21][N:20]=2)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:26][O-:27].[Na+]>CO>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([CH2:17][NH:18][C:19]2[C:24]([O:27][CH3:26])=[N:23][CH:22]=[CH:21][N:20]=2)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 10269934HCID 10269934, compoundHCID 10942334Sodium Methoxide

Product 1

HCID 23577286HCID 23577286, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-[(3-Chloro-pyrazin-2-ylamino)-methyl]-piperidine-1-carboxylic acid benzyl ester (2.72 g, 7.54 mmol) and 0.5 M sodium methoxide in methanol (40 mL) were heated under nitrogen at 60° C. for 2 days, cooled, evaporated and the residue partitioned between EtOAc and water. The organic layer was washed with brine, dried and solvent evaporated to afford crude material, purified by flash chromatography on silica (gradient 25 to 100% EtOAc hexane) to give the desired compound as a solid. The solid was stirred with approx. (10 mL) 2:1 isopropyl acetate:hexane and filtered to give the title compound as white solid. M.S.(M+1): 357.

Workup

  1. temperaturecooled
  2. customevaporated
  3. customthe residue partitioned between EtOAc and water
  4. washThe organic layer was washed with brine
  5. customdried
  6. customsolvent evaporated
  7. customto afford crude material
  8. custompurified by flash chromatography on silica (gradient 25 to 100% EtOAc hexane)

Sources & evidence

ORD record
ord-2c821cee580442c0a989b5a149e07fed
Source dataset
uspto-grants-2006_05
Patent number
US07053089B2

Reaction notes

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