Trifluoroacetic acid → HCID 71008950, compound

HRID 1887479Notes

Reaction equation

[CH2:1]([N:8]([CH2:12][Si](C)(C)C)[CH2:9]OC)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:17][C:18]([F:34])([F:33])[O:19][C:20]1[CH:25]=[CH:24][C:23]([N:26]2[CH2:31][CH2:30][CH:29]=[CH:28][C:27]2=[O:32])=[CH:22][CH:21]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[CH2:1]([N:8]1[CH2:9][CH:29]2[CH:28]([C:27](=[O:32])[N:26]([C:23]3[CH:22]=[CH:21][C:20]([O:19][C:18]([F:17])([F:34])[F:33])=[CH:25][CH:24]=3)[CH2:31][CH2:30]2)[CH2:12]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To N-benzyl(methoxy)-N-((trimethylsilyl)methyl)methanamine (1.7 g, 7.0 mmol) and 1-(4-trifluoromethoxy-phenyl)-5,6-dihydro-1H-pyridin-2-one (0.6 g, 2.3 mmol) in DCM (30 mL) was added a solution of trifluoroacetic acid (0.026 g, 0.23 mmol) in DCM (10 mL) at 4° C. After the mixture was stirred at 50° C. for 3 h, the solution was washed with saturated sodium bicarbonate and brine, then dried over anhydrous Na2SO4. After removal of the DCM, the residue was purified by column chromatography on silica gel with petroleum ether/ethyl acetate P (10:1 to 5:1) to yield the title compound (0.19 g, 21%). 1H NMR (300 MHz, CDCl3): δ 7.34-7.20 (m, 9H), 3.77-3.55 (m, 4H), 3.18-3.01 (m, 2H), 2.93-3.83 (m, 3H), 2.43-2.41 (m, 1H), 2.07-2.05 (m, 1H), 1.80-1.75 (m, 1H); LC-MS: [M+1]+ 391.1.

Workup

washthe solution was washed with saturated sodium bicarbonate and brine
dry with materialdried over anhydrous Na2SO4
customAfter removal of the DCM
customthe residue was purified by column chromatography on silica gel with petroleum ether/ethyl acetate P (10:1 to 5:1)

Sources & evidence

ORD record: ord-af21e24d68cd4c1888223403987272e5
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08501768B2

Reaction notes

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