Ethyl Acetate → 2-[(S)-4-Boc-3-benzylpiperazinyl]-6-chloropyrazine

HRID 643350Notes

Reaction equation

Cl[C:2]1[CH:7]=[N:6][CH:5]=[C:4]([Cl:8])[N:3]=1.[C:9]([N:16]1[CH2:21][CH2:20][NH:19][CH2:18][C@@H:17]1[CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10].C(N(C(C)C)CC)(C)C.C(OCC)(=O)C>O1CCOCC1.FC(C1C=CC=CC=1)(F)F>[C:9]([N:16]1[CH2:21][CH2:20][N:19]([C:2]2[CH:7]=[N:6][CH:5]=[C:4]([Cl:8])[N:3]=2)[CH2:18][C@@H:17]1[CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)([O:11][C:12]([CH3:14])([CH3:15])[CH3:13])=[O:10]

Participants

Conditions

Temperature: 180 °C

Procedure

To a solution of 2,6-dichloropyrazine 114 (0.1 g, 0.67 mmol.) and (S)-1-Boc-2-benzylpiperazine 107 (0.37 g, 1.34 mmol) in dioxane (2 mL) and trifluoromethylbenzene (2 mL) was added diisopropylethylamine (0.26 g, 2.0 mmol). The reaction mixture was heated in a microwave reactor at 180° C. for 20 minutes. Ethyl acetate (100 mL) was added. The organic layer was washed with saturated ammonium chloride solution, 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-[(S)-4-Boc-3-benzylpiperazinyl]-6-chloropyrazine 115 (0.234 g, 0.6 mmol).

Workup

washThe organic layer was washed with saturated ammonium chloride solution, 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 flash column chromatography

Sources & evidence

ORD record: ord-35c999faa8b149c0b7f7e03e38ab4980
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07700601B2

Reaction notes

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