Ethyl Acetate → 4-(2-Cyclopropylethoxy)-n-[2-[(2-hydroxyethyl)amino]-2-oxo-1-(4-propylbenzyl)ethyl]benzamide

HRID 1799231Notes

Reaction equation

HRID 1799231 reaction equation
CO.C1COCC1.[CH:8]1([CH2:11][CH2:12][O:13][C:14]2[CH:39]=[CH:38][C:17]([C:18]([NH:20]/[C:21](/[C:32]([NH:34][CH2:35][CH2:36][OH:37])=[O:33])=[CH:22]\[C:23]3[CH:28]=[CH:27][C:26]([CH:29]4[CH2:31][CH2:30]4)=[CH:25][CH:24]=3)=[O:19])=[CH:16][CH:15]=2)[CH2:10][CH2:9]1.C(OCC)(=O)C>C(#N)C.O.[C].[Pd]>[CH:8]1([CH2:11][CH2:12][O:13][C:14]2[CH:39]=[CH:38][C:17]([C:18]([NH:20][CH:21]([CH2:22][C:23]3[CH:28]=[CH:27][C:26]([CH2:29][CH2:30][CH3:31])=[CH:25][CH:24]=3)[C:32]([NH:34][CH2:35][CH2:36][OH:37])=[O:33])=[O:19])=[CH:16][CH:15]=2)[CH2:9][CH2:10]1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 21899815MeOH tetrahydrofuranHCID 576845604-(2-Cyclopropylethoxy)-N-((Z)-2-(4-cyclopropylphenyl)-1-{[(2-hydroxyethyl)amino]carbonyl}vinyl)benzamide2×

Product 1

HCID 579721504-(2-Cyclopropylethoxy)-n-[2-[(2-hydroxyethyl)amino]-2-oxo-1-(4-propylbenzyl)ethyl]benzamideYield 48%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

To a methanol:THF (2:1, V/V, 6 mL) solution of 4-(2-cyclopropylethoxy)-N-((Z)-2-(4-cyclopropylphenyl)-1-{[(2-hydroxyethyl)amino]carbonyl}vinyl)benzamide (215 mg, 0.495 mmol) prepared in Example (1 (1d) was added 10% palladium-carbon (wet, 100 mg). The mixture was stirred under a hydrogen atmosphere (rubber balloon) at room temperature for 2 hours. To the reaction solution was added ethyl acetate (10 mL), and the mixture was filtered. The solvent was evaporated, and the residue was purified by thin layer chromatography for separation (ethyl acetate, developed once) to give a white solid. This solid was suspended in acetonitrile:water (1:1, V/V, 4 mL), and the insoluble substance was collected by filtration, washed with water, and dried under reduced pressure to give 104 mg of the title compound (white powder, yield: 48%).

Workup

  1. filtrationthe mixture was filtered
  2. customThe solvent was evaporated
  3. customthe residue was purified by thin layer chromatography for separation (ethyl acetate
  4. customdeveloped once) to give a white solid
  5. filtrationthe insoluble substance was collected by filtration
  6. washwashed with water
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-ae221d732ef046aa8db736f06f6c914f
Source dataset
uspto-grants-2013_01
Patent number
US08344029B2

Reaction notes

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