Triethylamine → HCID 11685915, compound

HRID 1932544Notes

Reaction equation

HRID 1932544 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([C:14](=[O:35])[CH2:15][N:16]([CH3:34])[C:17]2[CH:22]=[CH:21][C:20]([O:23][C:24]3[CH:29]=[CH:28][C:27]([N+:30]([O-])=O)=[CH:26][N:25]=3)=[C:19]([CH3:33])[CH:18]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[F:43][C:44]([F:55])([F:54])[C:45]1[CH:53]=[CH:52][C:48]([C:49](Cl)=[O:50])=[CH:47][CH:46]=1.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C.[Pt].[C]>[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([C:14](=[O:35])[CH2:15][N:16]([CH3:34])[C:17]2[CH:22]=[CH:21][C:20]([O:23][C:24]3[N:25]=[CH:26][C:27]([NH:30][C:49](=[O:50])[C:48]4[CH:52]=[CH:53][C:45]([C:44]([F:43])([F:54])[F:55])=[CH:46][CH:47]=4)=[CH:28][CH:29]=3)=[C:19]([CH3:33])[CH:18]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 676074-(Trifluoromethyl)benzoyl chlorideHCID 516892Sodium BicarbonateHCID 68526882HCID 68526882, compound

Product 1

HCID 11685915HCID 11685915, compound

Reagents, catalysts & solvents 2

HCID 178503042HCID 178503042, compoundCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
40 °C

Procedure

To a suspension of 1-(4-benzylpiperazin-1-yl)-2-{methyl[3-methyl-4-(5-nitropyridin-2-yloxy)phenyl]amino}ethanone (2.85 g, 6.0 mmol) in ethyl acetate (30 mL) was added 5% platinum-carbon (0.30 g) under a nitrogen atmosphere, and the resulting solution was stirred for 3 hours at 40° C. under a hydrogen atmosphere. The platinum-carbon was separated off with Celite, and the filtrate was concentrated. The residue was dissolved in THF (30 mL), and to this solution was added triethylamine (1.26 mL, 9.1 mmol) under ice cooling. To the resulting solution was then added dropwise 4-(trifluoromethyl)benzoyl chloride (1.16 mL, 7.8 mmol). This reaction solution was stirred overnight, then a saturated sodium bicarbonate solution was added, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with water, and then dried over anhydrous sodium sulfate. The solvent was evaporated, and the residue was purified by silica gel column chromatography (dichloromethane:methanol=20:1). The resulting product was then recrystallized from a mixed solvent consisting of diisopropyl ether-acetone, to thereby yield 1.37 g of the title compound.

Workup

  1. customThe platinum-carbon was separated off with Celite
  2. concentrationthe filtrate was concentrated
  3. dissolutionThe residue was dissolved in THF (30 mL)
  4. stirringThis reaction solution was stirred overnight
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe ethyl acetate layer was washed with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. customThe solvent was evaporated
  9. customthe residue was purified by silica gel column chromatography (dichloromethane:methanol=20:1)
  10. customThe resulting product was then recrystallized from a mixed solvent

Sources & evidence

ORD record
ord-b52599c4b7bb43edbec07b70c3010d34
Source dataset
uspto-grants-2012_05
Patent number
US08188277B2

Reaction notes

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