Methyl vinyl sulfone → HCID 86625196, compound

HRID 419533Notes

Reaction equation

C(O)(=O)C.[F:5][C:6]([F:26])([F:25])[C:7]([NH:9][C:10]1[CH:15]=[C:14]([CH3:16])[C:13]([CH:17]2[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]2)=[CH:12][C:11]=1[O:23][CH3:24])=[O:8].[CH:27]([S:29]([CH3:32])(=[O:31])=[O:30])=[CH2:28]>O1CCOCC1>[F:26][C:6]([F:5])([F:25])[C:7]([NH:9][C:10]1[CH:15]=[C:14]([CH3:16])[C:13]([CH:17]2[CH2:22][CH2:21][N:20]([CH2:28][CH2:27][S:29]([CH3:32])(=[O:31])=[O:30])[CH2:19][CH2:18]2)=[CH:12][C:11]=1[O:23][CH3:24])=[O:8]

Participants

Conditions

Temperature: 90 °C

Procedure

To 2,2,2-trifluoro-N-[5-methyl-2-(methyloxy)-4-(4-piperidinyl)phenyl]acetamide acetate (1.5 g, 4.0 mmol) in 30 mL of dioxane was added, TEA (2 g, 20 mmol), and methyl vinyl sulfone (1.06 g, 10 mmol). The mixture was heated to 90° C. for 72 h. The solvent was rotovaped down and the crude product was purified by flash chromatography to give 480 mg of 2,2,2-trifluoro-N-(5-methyl-2-(methyloxy)-4-{1-[2-(methylsulfonyl)ethyl]-4-piperidinyl}phenyl)acetamide and the title compound of step D (0.40 g, 1.2 mmol, 31%). 1H NMR (400 MHz, CDCl3) δ ppm 6.62 (s, 1H), 6.51 (s, 1H), 5.22 (s, 2H), 3.80 (bs, 3H), 3.29 (t, J=6.87 Hz, 2H), 3.13 (d, J=11.17 Hz, 2H), 3.04 (s, 3H), 2.98 (t, J=6.96 Hz, 2H), 2.61-2.70 (m, 1H), 2.24-2.31 (m, 2H), 2.17 (s, 3H), 1.73-1.81 (m, 4H).

Workup

customthe crude product was purified by flash chromatography

Sources & evidence

ORD record: ord-f52244db8e454390a60994281952ee8c
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08093239B2

Reaction notes

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