Trifluoroacetic acid → HCID 71008634, compound

HRID 1887489Notes

Reaction equation

HRID 1887489 reaction equation
FC(F)(F)C(O)=O.[F:8][C:9]([F:25])([F:24])[O:10][C:11]1[CH:16]=[CH:15][C:14]([N:17]2[C:21](=[O:22])[CH:20]=[CH:19][C:18]2=[O:23])=[CH:13][CH:12]=1.CO[CH2:28][N:29]([CH2:37][Si](C)(C)C)[CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>ClCCl>[CH2:30]([N:29]1[CH2:37][CH:19]2[C:18](=[O:23])[N:17]([C:14]3[CH:15]=[CH:16][C:11]([O:10][C:9]([F:8])([F:24])[F:25])=[CH:12][CH:13]=3)[C:21](=[O:22])[CH:20]2[CH2:28]1)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 353442Benzyl(methoxymethyl)((trimethylsilyl)methyl)amineHCID 6768261-[4-(Trifluoromethoxy)phenyl]-1H-pyrrole-2,5-dione

Product 1

HCID 71008634HCID 71008634, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of trifluoroacetic acid (0.89 g, 0.78 mmol) in dichloromethane was added at 4° C. to a stirred solution of 1-(4-(trifluoromethoxy)phenyl)-1H-pyrrole-2,5-dione (2.0 g, 7.8 mmol) and N-(methoxymethyl)(phenyl)-N-((trimethylsilyl)methyl)methanamine (2.2 g, 9.3 mmol) in dichloromethane (100 mL). After 3 h at room temperature, the solution was washed with saturated sodium bicarbonate (80 mL) and brine (80 mL) and dried over Na2SO4. After removal of dichloromethane, the residue was purified by column chromatography on silica gel with petroleum ether:ethyl acetate (10:1 to 5:1) to yield the title compound (2.8 g, 90%). 1H NMR (300 MHz, CDCl3): δ 7.46-7.41 (m, 5H), 7.38-7.31 (m, 4H), 4.19 (s, 2H), 3.89-3.87 (m, 2H), 3.67-3.65 (m, 2H), 3.21 (bs, 2H), LC-MS: [M+1]+ 390.9.

Workup

  1. washthe solution was washed with saturated sodium bicarbonate (80 mL) and brine (80 mL)
  2. dry with materialdried over Na2SO4
  3. customAfter removal of dichloromethane
  4. customthe residue was purified by column chromatography on silica gel with petroleum ether:ethyl acetate (10:1 to 5:1)

Sources & evidence

ORD record
ord-aee7a4c8b5c045aabe43c1cacc300a0e
Source dataset
uspto-grants-2013_08
Patent number
US08501768B2

Reaction notes

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