1-Methylpiperazine → HCID 66797580, compound

HRID 1020749Notes

Reaction equation

[C:1]([O:5][C:6]([NH:8][C@@H:9]([C:11]1[CH:12]=[C:13](OS(C(F)(F)F)(=O)=O)[CH:14]=[CH:15][CH:16]=1)[CH3:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:25][N:26]1[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1.C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.C(OCC)(=O)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:1]([O:5][C:6](=[O:7])[NH:8][C@@H:9]([C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([N:29]2[CH2:30][CH2:31][N:26]([CH3:25])[CH2:27][CH2:28]2)[CH:12]=1)[CH3:10])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of Trifluoro-methanesulfonic acid 3-((R)-1-tert-butoxycarbonylamino-ethyl)-phenyl ester (0.340 g, 0.921 mmol), 1-methylpiperazine (0.37 g, 3.68 mmol), Pd2(dba)3 (0.042 g, 0.046 mmol), 2-(di-tert-butylphosphino)-biphenyl (0.054 g, 0.184 mmol), and potassium phosphate (0.273 g, 1.29 mmol) in 20 mL of 1,4 dioxane was heated at 80° C. in a sealed tube for 12 hours. After completion of the reaction, the reaction mixture was cooled to room temperature and diluted with ethyl acetate (100 mL) and the washed with water (20 mL). The aqueous layer was extracted with ethyl acetate (2×50 mL), and the combined organic layers were dried over magnesium sulfate and concentrated in vacuo to afford the crude title compound.

Workup

customAfter completion of the reaction
temperaturethe reaction mixture was cooled to room temperature
washthe washed with water (20 mL)
extractionThe aqueous layer was extracted with ethyl acetate (2×50 mL)
dry with materialthe combined organic layers were dried over magnesium sulfate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-8a0944a007084383b548351bbb5f7d59
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08716473B2

Reaction notes

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