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

HRID 643345ノート

反応式

HRID 643345 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 7368(Trifluoromethyl)benzene溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
210 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-9bd9fd703c5b4e71849920b50ddf04d1
出典データセット
uspto-grants-2010_04
特許番号
US07700601B2

反応ノート

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