HCID 56999119, compound → HCID 57253835, compound

HRID 584245Notes

Reaction equation

HRID 584245 reaction equation
[F:1][C:2]([F:44])([F:43])[C:3]1[CH:4]=[C:5]([CH:36]=[C:37]([C:39]([F:42])([F:41])[F:40])[CH:38]=1)[C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]#[C:16][CH2:17][N:18]2[CH2:23][CH2:22][O:21][CH2:20][C@@H:19]2[CH2:24][O:25][CH3:26])[CH2:10][C@H:9]1[CH2:27][C:28]1[CH:33]=[CH:32][C:31]([CH3:34])=[C:30]([CH3:35])[CH:29]=1)=[O:7]>CO.[C].[Pd]>[F:44][C:2]([F:1])([F:43])[C:3]1[CH:4]=[C:5]([CH:36]=[C:37]([C:39]([F:40])([F:42])[F:41])[CH:38]=1)[C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][CH2:17][N:18]2[CH2:23][CH2:22][O:21][CH2:20][C@@H:19]2[CH2:24][O:25][CH3:26])[CH2:10][C@H:9]1[CH2:27][C:28]1[CH:33]=[CH:32][C:31]([CH3:34])=[C:30]([CH3:35])[CH:29]=1)=[O:7]

Participants

4

Reactant 1

HCID 56999119HCID 56999119, compound

Product 1

HCID 57253835HCID 57253835, compound

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

A solution of (2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(3,4-dimethylbenzyl)-4-[4-((3S)-3-methoxymethylmorpholino)-2-butynyl]piperazine (0.09 g) in methanol (10 ml) was hydrogenated in the presence of 10% palladium-carbon (40 mg) at room temperature. After 1 hour, palladium-carbon was removed by filtration and the filtrate was evaporated under reduced pressure. The residue was purified by column chromatography on silica gel with a mixture of methanol and ethyl acetate as an eluent to give (2R)-1-[3,5-bis-(trifluoromethyl)benzoyl]-2-(3,4-dimethylbenzyl)-4-[4-((3S)-3-methoxymethylmorpholino)butyl]piperazine. It was dissolved in ethyl acetate (10 ml) and 4N hydrogen chloride in ethyl acetate (0.5 ml) was added thereto. The mixture was evaporated in vacuo and the residue was triturated with a mixture of ethyl acetate and isopropyl ether to give (2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(3,4-dimethylbenzyl)-4-[4-((3S)-3-methoxymethylmorpholino)butyl]piperazine dihydrochloride (0.03 g) as a solid.

Workup

  1. custompalladium-carbon was removed by filtration
  2. customthe filtrate was evaporated under reduced pressure
  3. customThe residue was purified by column chromatography on silica gel with a mixture of methanol and ethyl acetate as an eluent

Sources & evidence

ORD record
ord-5c0547f4c12e4b0b95a05497fc21f677
Source dataset
uspto-grants-2005_08
Patent number
US06924278B2

Reaction notes

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