HCID 59511421, compound → HCID 59511436, compound

HRID 1157585Notes

Reaction equation

HRID 1157585 reaction equation
[CH3:1][N:2]([CH3:22])[CH2:3][CH2:4][N:5]([CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([N+:19]([O-])=O)[CH:14]=1)[C:6](=[O:11])[C:7]([F:10])([F:9])[F:8]>CC(O)C.[Pd]>[NH2:19][C:15]1[CH:14]=[C:13]([CH2:12][N:5]([CH2:4][CH2:3][N:2]([CH3:22])[CH3:1])[C:6](=[O:11])[C:7]([F:8])([F:9])[F:10])[CH:18]=[CH:17][CH:16]=1

Participants

4

Reactant 1

HCID 59511421HCID 59511421, compound

Product 1

HCID 59511436HCID 59511436, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 3776IsopropanolSolvent

Procedure

To a solution of N-[2-(dimethylamino)ethyl]-2,2,2-trifluoro-N-[(3-nitrophenyl)methyl]acetamide (204 mg, 0.64 mmol) in i-PrOH was added 10% Pd/C (20 mg, 0.02 mmol). A balloon charged with H2 was installed, and the reaction was stirred at rt under a hydrogen atmosphere. After 17 h, the reaction mixture was filtered through celite and adsorbed onto silica gel. The crude product was purified by column chromatography to generate the title compound in 62% yield. 1H NMR (400 MHz, CDCl3) δ 7.10 (t, J=7.9 Hz, 1H), 6.69-6.70 (m, 2H), 6.58 (d, J=7.9 Hz, 1H), 3.76 (s, 2H), 2.75 (t, J=6.0 Hz, 2H), 2.49 (t, J=6.0 Hz, 2H), 2.24 (s, 6H). ES-LC/MS m/z=290 [M+H]+.

Workup

  1. additionA balloon charged with H2
  2. filtrationthe reaction mixture was filtered through celite
  3. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-cc0d4aefd5c343febd1ce0d5d1ecdd26
Source dataset
uspto-grants-2010_10
Patent number
US07807673B2

Reaction notes

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