Triethylamine → HCID 178525136, compound

HRID 1351504Notes

Reaction equation

HRID 1351504 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([CH2:7][NH:8][C:9]2[C:10]([OH:15])=[N:11][CH:12]=[CH:13][N:14]=2)[CH2:3][CH2:2]1.C(N(CC)CC)C.[CH2:23]([O:30][C:31](ON1C(=O)CCC1=O)=[O:32])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>CN(C=O)C>[CH2:23]([O:30][C:31]([N:1]1[CH2:6][CH2:5][CH:4]([CH2:7][NH:8][C:9]2[C:10]([OH:15])=[N:11][CH:12]=[CH:13][N:14]=2)[CH2:3][CH2:2]1)=[O:32])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 83172Benzyl succinimido carbonateHCID 178517836HCID 178517836, compound

Product 1

HCID 178525136HCID 178525136, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-[(piperidin-4-ylmethyl)-amino]-pyrazin-2-ol from Step 1 above (0.287 g, 1.021 mmol) in DMF (5 mL) was added triethylamine (0.356 mL, 2.55 mmol), followed by N-(benzyloxycarbonyloxy)succinimide (0.305 g, 1.23 mmol). The resulting reaction mixture was stirred at rt for 15 min, then partitioned between EtOAc and water. The organic layer was washed with water and brine, dried over anhydrous sodium sulfate and the crude product purified by flash column chromatography (50% EtOAc hexane to 5% MeOH EtOAc) to give an oil which solidified on standing. M.S (M+1): 343.24.

Workup

  1. customThe resulting reaction mixture
  2. custompartitioned between EtOAc and water
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe crude product purified by flash column chromatography (50% EtOAc hexane to 5% MeOH EtOAc)
  6. customto give an oil which

Sources & evidence

ORD record
ord-367947f0658b4424bf23bba2ddc21176
Source dataset
uspto-grants-2007_05
Patent number
US07217716B2

Reaction notes

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