Trifluoroacetic acid → HCID 71008325, compound

HRID 1887486Notes

Reaction equation

[F:1][C:2]([F:19])([F:18])[CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:16][CH2:15][CH:14]=[CH:13][C:12]2=[O:17])=[CH:7][CH:6]=1.[CH2:20]([N:27]([CH2:31][Si](C)(C)C)[CH2:28]OC)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:20]([N:27]1[CH2:31][CH:14]2[CH:13]([C:12](=[O:17])[N:11]([C:8]3[CH:9]=[CH:10][C:5]([O:4][CH2:3][C:2]([F:1])([F:18])[F:19])=[CH:6][CH:7]=3)[CH2:16][CH2:15]2)[CH2:28]1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

Conditions

Temperature: 45 °C

Procedure

A mixture of 1-[4-(2,2,2-Trifluoro-ethoxy)-phenyl]-5,6-dihydro-1H-pyridin-2-one (0.27 g, 0.1 mmol), N-benzyl(methoxy)-N-((trimethylsilyl)methyl)methanamine (0.71 g, 0.3 mmol) and TFA (0.114 g, 0.1 mmol) in 20 mL of DCM was stirred at 45° C. for 30 h. The mixture was evaporated to dryness and the residue was purified by silica-gel column chromatography (eluting with petroleum ether/ethyl acetate=1:1) to obtain the title compound as colorless oil (0.125 g, 31%). LC-MS: 405.2 [M+1]+.

Workup

customThe mixture was evaporated to dryness
customthe residue was purified by silica-gel column chromatography (eluting with petroleum ether/ethyl acetate=1:1)

Sources & evidence

ORD record: ord-7e12cb7776ae4f648ec895ac970768d3
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08501768B2

Reaction notes

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