Ethyl Acetate → 2-amino-5-bromo-3-[(S)-4-Boc-3-benzylpiperazinyl]pyrazine

HRID 643345노트

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HRID 643345 반응식
[NH2:1][C:2]1[C:7](Br)=[N:6][C:5]([Br:9])=[CH:4][N:3]=1.[C:10]([N:17]1[CH2:22][CH2:21][NH:20][CH2:19][C@@H:18]1[CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11].C(N(C(C)C)CC)(C)C.C(OCC)(=O)C>O1CCOCC1.FC(C1C=CC=CC=1)(F)F>[NH2:1][C:2]1[C:7]([N:20]2[CH2:21][CH2:22][N:17]([C:10]([O:12][C:13]([CH3:15])([CH3:16])[CH3:14])=[O:11])[C@@H:18]([CH2:23][C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[CH2:19]2)=[N:6][C:5]([Br:9])=[CH:4][N:3]=1

참가 물질

7

반응물 4

HCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 6200042-Amino-3,5-dibromopyrazineHCID 177504411,1-Dimethylethyl (2S)-2-(phenylmethyl)-1-piperazinecarboxylate

생성물 1

HCID 592622472-amino-5-bromo-3-[(S)-4-Boc-3-benzylpiperazinyl]pyrazine수율 67.8%

시약·촉매·용매 2

HCID 7368(Trifluoromethyl)benzene용매HCID 312751,4-Dioxane용매

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온도
210 °C

실험 절차

To a solution of 2-amino-3,5-dibromopyrazine 106 (0.2 g, 0.79 mmol.) and (S)-1-Boc-2-benzylpiperazine 107 (0.44 g, 1.59 mmol) in dioxane (2 mL) and trifluoromethylbenzene (2 mL) was added diisopropylethylamine (0.31 g, 2.4 mmol). The reaction mixture was heated in a microwave reactor at 210° C. for 20 minutes. 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 2-amino-5-bromo-3-[(S)-4-Boc-3-benzylpiperazinyl]pyrazine 108 (0.24 g, 0.536 mmol).

후처리

  1. washThe organic layer was washed with water and brine
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. customThe organic solvent was evaporated under reduced pressure
  4. customThe crude product was purified by RP-HPLC

출처 및 근거

ORD 기록
ord-9bd9fd703c5b4e71849920b50ddf04d1
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07700601B2

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