[5-Ethynyl-2-(3-hexyl-phenyl)-3-methyl-3H-imidazol-4-yl]-(4-pyrrolidin-1-yl-piperidin-1-yl)-methanone → [5-Ethyl-2-(3-hexyl-phenyl)-3-methyl-3H-imidazol-4-yl]-(4-pyrrolidin-1-yl-piperidin-1-yl)-methanone

HRID 545377Notes

Reaction equation

HRID 545377 reaction equation
[C:1]([C:3]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH:9]=2)[N:5]([CH3:20])[C:4]=1[C:21]([N:23]1[CH2:28][CH2:27][CH:26]([N:29]2[CH2:33][CH2:32][CH2:31][CH2:30]2)[CH2:25][CH2:24]1)=[O:22])#[CH:2]>CO.[Pd]>[CH2:1]([C:3]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH:9]=2)[N:5]([CH3:20])[C:4]=1[C:21]([N:23]1[CH2:28][CH2:27][CH:26]([N:29]2[CH2:30][CH2:31][CH2:32][CH2:33]2)[CH2:25][CH2:24]1)=[O:22])[CH3:2]

Participants

4

Reactant 1

HCID 57541130[5-Ethynyl-2-(3-hexyl-phenyl)-3-methyl-3H-imidazol-4-yl]-(4-pyrrolidin-1-yl-piperidin-1-yl)-methanone

Product 1

HCID 57541140[5-Ethyl-2-(3-hexyl-phenyl)-3-methyl-3H-imidazol-4-yl]-(4-pyrrolidin-1-yl-piperidin-1-yl)-methanoneYield 92%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 0.13 g (0.29 mmol) of [5-ethynyl-2-(3-hexyl-phenyl)-3-methyl-3H-imidazol-4-yl]-(4-pyrrolidin-1-yl-piperidin-1-yl)-methanone (example 13) in 5 ml of MeOH was treated with 0.031 g (0.03 mmol) of Pd—C (10%) and the reaction mixture was then hydrogenated with H2 (1 bar) at RT for 2 hours. After removal the catalyst by filtration, the solvent was evaporated. The residue was purified by flash column chromatography (CH2Cl2/MeOH 1:0 to 4:1) to give 0.12 g (92%) of the title compound as light yellow oil. MS: 451.1 (MH+).

Workup

  1. customAfter removal the catalyst
  2. filtrationby filtration
  3. customthe solvent was evaporated
  4. customThe residue was purified by flash column chromatography (CH2Cl2/MeOH 1:0 to 4:1)

Sources & evidence

ORD record
ord-561b7c2f7734465ba41b5b53672687aa
Source dataset
uspto-grants-2011_05
Patent number
US07935707B2

Reaction notes

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