Benzyl Bromide → 2-benzylamino-3-[(S)-4-Boc-3-benzylpiperazinyl]-5-bromopyrazine

HRID 643349Notes

Reaction equation

HRID 643349 reaction equation
[NH2:1][C:2]1[C:7]([N:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[C@@H:10]([CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH2:9]2)=[N:6][C:5]([Br:28])=[CH:4][N:3]=1.CC(C)([O-])C.[K+].[CH2:35](Br)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1.C(OCC)(=O)C>O1CCOCC1>[CH2:35]([NH:1][C:2]1[C:7]([N:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:19])([CH3:20])[CH3:18])=[O:15])[C@@H:10]([CH2:21][C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH2:9]2)=[N:6][C:5]([Br:28])=[CH:4][N:3]=1)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Participants

6

Reactant 4

HCID 7498Benzyl BromideHCID 8857Ethyl AcetateHCID 23665647Potassium tert-butoxideHCID 592622472-amino-5-bromo-3-[(S)-4-Boc-3-benzylpiperazinyl]pyrazine

Product 1

HCID 592622612-benzylamino-3-[(S)-4-Boc-3-benzylpiperazinyl]-5-bromopyrazineYield 81%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 2-amino-5-bromo-3-[(S)-4-Boc-3-benzylpiperazinyl]pyrazine 108 (170 mg, 0.379 mmol) in anhydrous dioxane (3 mL) was added a 1 M solution of potassium t-butoxide (0.42 mL, 0.42 mmol). The reaction mixture was stirred at room temperature for 10 minutes and benzyl bromide (130 mg, 0.76 mmol) was added. The reaction mixture was stirred at room temperature for 2 hours. Ethyl acetate (100 mL) was added. The organic layer was washed with water and brine. The organic layer was dried over sodium sulfate. The organic solvent was evaporated under reduced pressure. The crude product was purified by flash column chromatography to yield the desired 2-benzylamino-3-[(S)-4-Boc-3-benzylpiperazinyl]-5-bromopyrazine 112 (165 mg, 0.307 mmol).

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 2 hours
  2. washThe organic layer was washed with water and brine
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. customThe organic solvent was evaporated under reduced pressure
  5. customThe crude product was purified by flash column chromatography

Sources & evidence

ORD record
ord-3686c48d0af94dc1a3f47116f4151ce8
Source dataset
uspto-grants-2010_04
Patent number
US07700601B2

Reaction notes

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