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

HRID 643345Notes

Reaction equation

[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

Participants

Conditions

Temperature: 210 °C

Procedure

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).

Workup

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

Sources & evidence

ORD record: ord-9bd9fd703c5b4e71849920b50ddf04d1
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07700601B2

Reaction notes

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