Hydrogen chloride-ethyl acetate → HCID 71252826, compound

HRID 2411722Notes

Reaction equation

HRID 2411722 reaction equation
[CH3:1][C:2]1[C:3]([N:9]2[CH2:14][CH2:13][N:12]([C:15]([C:17]3[CH:22]=[CH:21][C:20]([N:23]4[CH:27]([CH3:28])[CH2:26][CH2:25][C:24]4=[O:29])=[CH:19][C:18]=3[N:30]3[CH2:34][CH2:33][CH2:32][C:31]3=[O:35])=[O:16])[CH2:11][CH2:10]2)=[N:4][CH:5]=[C:6]([CH3:8])[CH:7]=1.[ClH:36].C(OCC)(=O)C>C(OCC)(=O)C>[ClH:36].[CH3:1][C:2]1[C:3]([N:9]2[CH2:14][CH2:13][N:12]([C:15]([C:17]3[CH:22]=[CH:21][C:20]([N:23]4[CH:27]([CH3:28])[CH2:26][CH2:25][C:24]4=[O:29])=[CH:19][C:18]=3[N:30]3[CH2:34][CH2:33][CH2:32][C:31]3=[O:35])=[O:16])[CH2:11][CH2:10]2)=[N:4][CH:5]=[C:6]([CH3:8])[CH:7]=1

Participants

4

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 71252827HCID 71252827, compound

Product 1

HCID 71252826HCID 71252826, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

tris(dibenzylideneacetone)dipalladium(0)-chloroform adduct (55 mg) and 2-di-tert-butylphosphino-3,4,5,6-tetramethyl-2′,4′,6′-triisopropyl-1,1′-biphenyl (26 mg) was added toluene (1 mL), and the mixture was stirred with heating under reflux for 8 hr. The reaction mixture was cooled, water was added, and the mixture was extracted with ethyl acetate, and the solvent was evaporated. The obtained residue was purified by column chromatography (ethyl acetate:methanol) to give 1-{4-[4-(3,5-dimethylpyridin-2-yl)piperazine-1-carbonyl]-3-(2-oxopyrrolidin-1-yl)phenyl}-5-methylpyrrolidin-2-one. The obtained 1-{4-[4-(3,5-dimethylpyridin-2-yl)piperazine-1-carbonyl]-3-(2-oxopyrrolidin-1-yl)phenyl}-5-methylpyrrolidin-2-one was dissolved in ethyl acetate, 4N hydrogen chloride/ethyl acetate (0.13 mL) was added, and the precipitate was collected by filtration to give the title compound (37 mg).

Workup

  1. filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record
ord-ed57dd248c474949947b543126f76dc2
Source dataset
uspto-grants-2014_08
Patent number
US08816079B2

Reaction notes

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