Potassium Carbonate → HCID 10341498, compound

HRID 1295707Notes

Reaction equation

[CH2:1](OS(C)(=O)=O)[CH2:2][CH2:3][CH3:4].[N:10]1([C:16]2[C:17](=[O:34])[N:18]([CH2:22][CH2:23][O:24][C:25]3[CH:30]=[C:29]([F:31])[C:28]([F:32])=[CH:27][C:26]=3[F:33])[CH:19]=[CH:20][N:21]=2)[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1.Cl.N1(C2C(=O)N(CCOC3C=C(F)C(F)=CC=3F)C=CN=2)CCNCC1.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.CCOC(C)=O.O>[F:33][C:26]1[CH:27]=[C:28]([F:32])[C:29]([F:31])=[CH:30][C:25]=1[O:24][CH2:23][CH2:22][N:18]1[CH:19]=[CH:20][N:21]=[C:16]([N:10]2[CH2:15][CH2:14][N:13]([CH2:1][CH2:2][CH2:3][CH3:4])[CH2:12][CH2:11]2)[C:17]1=[O:34]

Participants

Conditions

Temperature: 60 °C

Procedure

Methanesulfonic acid butyl ester (0.30 g, 1.97 mmol; from Step 1) was added to a mixture of 3-(1-piperazinyl)-1-[2-(2,4,5-trifluorophenoxy)ethyl]-2(1H)-pyrazinone (0.50 g, 1.4 mmol; from the free base of Example 3) and potassium carbonate (0.10 g, 2.89 mmol) in DMSO (3 g). After being stirred for 3 h at 60° C., water (50 g) and EtOAc (100 g) were added to the reaction mixture. The layers were separated and the organic layer was concentrated in vacuo. The residue was purified by chromatography on a MPLC column using a continuous gradient (0-100% EtOAc in heptane) as eluent. This furnished 33 mg (8%) of the title compound as an oil. 1H NMR analysis supports the stated structure. HPLC purity: 100%. HRMS m/z calcd for C20H25F3N4O2 (M)+ 410.1930, found 410.1920.

Workup

customThe layers were separated
concentrationthe organic layer was concentrated in vacuo
customThe residue was purified by chromatography on a MPLC column

Sources & evidence

ORD record: ord-e120de0d0b314f13974855f291628d6c
Source dataset: uspto-grants-2007_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07244722B2

Reaction notes

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