Potassium Carbonate → [1-[2-[3-(3,4-Dichlorophenyl)-1-(3,4,5-trimethoxybenzoyl)pyrrolidin-3-yl]ethyl]piperidin-4-yl]-[1-[(4-fluorophenyl)methyl]benzimidazol-2-yl]methanone

HRID 2269842Notes

Reaction equation

HRID 2269842 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:27]=[C:28]([O:32][CH3:33])[C:29]=1[O:30][CH3:31])[C:6]([N:8]1[CH2:12][CH2:11][C:10]([C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[C:21]([Cl:26])[CH:20]=2)([CH2:13][CH2:14]S(C)(=O)=O)[CH2:9]1)=[O:7].[F:34][C:35]1[CH:58]=[CH:57][C:38]([CH2:39][N:40]2[C:44]3[CH:45]=[CH:46][CH:47]=[CH:48][C:43]=3[N:42]=[C:41]2[C:49]([CH:51]2[CH2:56][CH2:55][NH:54][CH2:53][CH2:52]2)=[O:50])=[CH:37][CH:36]=1.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C.CO>C1(C)C=CC=CC=1.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:27]=[C:28]([O:32][CH3:33])[C:29]=1[O:30][CH3:31])[C:6]([N:8]1[CH2:12][CH2:11][C:10]([CH2:13][CH2:14][N:54]2[CH2:55][CH2:56][CH:51]([C:49]([C:41]3[N:40]([CH2:39][C:38]4[CH:37]=[CH:36][C:35]([F:34])=[CH:58][CH:57]=4)[C:44]4[CH:45]=[CH:46][CH:47]=[CH:48][C:43]=4[N:42]=3)=[O:50])[CH2:52][CH2:53]2)([C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[C:21]([Cl:26])[CH:20]=2)[CH2:9]1)=[O:7]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 155428834-(1-(4-fluorobenzyl)-1H-benzimidazole-2-carbonyl)piperidineHCID 155428861-(3,4,5-Trimethoxy-benzoyl)-3-(3,4-dichloro-phenyl)-3-(2-methanesulfonyl-ethyl)-pyrrolidineHCID 21584119Ethylacetate methanol

Product 1

HCID 10190770[1-[2-[3-(3,4-Dichlorophenyl)-1-(3,4,5-trimethoxybenzoyl)pyrrolidin-3-yl]ethyl]piperidin-4-yl]-[1-[(4-fluorophenyl)methyl]benzimidazol-2-yl]methanone

Reagents, catalysts & solvents 1

HCID 22272177Toluene waterSolvent

Procedure

Combine 1-(3,4,5-trimethoxy-benzoyl)-3-(3,4-dichloro-phenyl)-3-(2-methanesulfonyl-ethyl)-pyrrolidine (0.26 g, 0.488 mmol) and 4-[1-(4-fluoro-benzyl)-1 H-benzoimidazole-2-carbonyl]-piperidine (0.25 g, 0.73 mmol), and potassium carbonate (0.20 g, 1.46 mmol) in toluene/water (10/1)(5 mL). Heat to reflux. After 3 days, cool and evaporate in vacuo to obtain a residue. Partition the residue between dichloromethane and water. Dry the organic layer over Na2SO4, filter, and concentrate in vacuo to obtain a residue. Chromatograph the residue on silica gel eluting with 10/1 ethyl acetate/methanol to give the title compound: Rf=0.28 (silica gel, 10/1 ethyl acetate/methanol).

Workup

  1. temperatureHeat to reflux
  2. temperaturecool
  3. customevaporate in vacuo
  4. customto obtain a residue
  5. customPartition the residue between dichloromethane and water
  6. dry with materialDry the organic layer over Na2SO4
  7. filtrationfilter
  8. concentrationconcentrate in vacuo
  9. customto obtain a residue

Sources & evidence

ORD record
ord-297dee41a1984185bc51597bac2b3126
Source dataset
uspto-grants-2001_12
Patent number
US06329392B1

Reaction notes

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