Methyl iodide → 3-[(S)4-Boc-3-benzylpiperazinyl]-5-bromo-2-methylaminopyrazine

HRID 643348노트

반응식

HRID 643348 반응식
[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.[CH3:29]C(C)([O-])C.[K+].IC.C(OCC)(=O)C>O1CCOCC1>[C:14]([N:11]1[CH2:12][CH2:13][N:8]([C:7]2[C:2]([NH:1][CH3:29])=[N:3][CH:4]=[C:5]([Br:28])[N:6]=2)[CH2:9][C@@H:10]1[CH2:21][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)([O:16][C:17]([CH3:19])([CH3:20])[CH3:18])=[O:15]

참가 물질

6

반응물 4

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 23665647Potassium tert-butoxideHCID 592622472-amino-5-bromo-3-[(S)-4-Boc-3-benzylpiperazinyl]pyrazine

생성물 1

HCID 592622593-[(S)4-Boc-3-benzylpiperazinyl]-5-bromo-2-methylaminopyrazine수율 309.9%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

To a solution of 2-amino-5-bromo-3-[(S)4-Boc-3-benzylpiperazinyl]pyrazine 108 (140 mg, 0.313 mmol) in anhydrous dioxane (3 mL) was added a 1 M solution of potassium t-butoxide (0.34 mL, 0.34 mmol). The reaction mixture was stirred at room temperature for 10 minutes and iodomethane (89 mg, 0.627 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 RP-HPLC to yield the desired 3-[(S)-4-Boc-3-benzylpiperazinyl]-5-bromo-2-methylaminopyrazine 111 (45 mg, 0.97 mmol).

후처리

  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 RP-HPLC

출처 및 근거

ORD 기록
ord-cc81edb18aba4267b8396430a206b9dc
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07700601B2

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