Diisopropylethylamine → [1-[(4-Fluorophenyl)methyl]benzimidazol-2-yl]-[1-[2-[3-phenyl-1-(3,4,5-trimethoxybenzoyl)pyrrolidin-3-yl]ethyl]piperidin-4-yl]methanone

HRID 2269850Notes

Reaction equation

HRID 2269850 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:25]=[C:26]([O:30][CH3:31])[C:27]=1[O:28][CH3:29])[C:6]([N:8]1[CH2:12][CH2:11][C:10]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)([CH2:13][CH2:14]S(C)(=O)=O)[CH2:9]1)=[O:7].[F:32][C:33]1[CH:56]=[CH:55][C:36]([CH2:37][N:38]2[C:42]3[CH:43]=[CH:44][CH:45]=[CH:46][C:41]=3[N:40]=[C:39]2[C:47]([CH:49]2[CH2:54][CH2:53][NH:52][CH2:51][CH2:50]2)=[O:48])=[CH:35][CH:34]=1.C(N(C(C)C)CC)(C)C.C(OCC)(=O)C.CO>ClC1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:25]=[C:26]([O:30][CH3:31])[C:27]=1[O:28][CH3:29])[C:6]([N:8]1[CH2:12][CH2:11][C:10]([CH2:13][CH2:14][N:52]2[CH2:53][CH2:54][CH:49]([C:47]([C:39]3[N:38]([CH2:37][C:36]4[CH:35]=[CH:34][C:33]([F:32])=[CH:56][CH:55]=4)[C:42]4[CH:43]=[CH:44][CH:45]=[CH:46][C:41]=4[N:40]=3)=[O:48])[CH2:50][CH2:51]2)([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:9]1)=[O:7]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 155428834-(1-(4-fluorobenzyl)-1H-benzimidazole-2-carbonyl)piperidineHCID 155428881-(3,4,5-Trimethoxy-benzoyl)-3-phenyl-3-(2-methanesulfonyl-ethyl)-pyrrolidineHCID 21584119Ethylacetate methanol

Product 1

HCID 10212223[1-[(4-Fluorophenyl)methyl]benzimidazol-2-yl]-[1-[2-[3-phenyl-1-(3,4,5-trimethoxybenzoyl)pyrrolidin-3-yl]ethyl]piperidin-4-yl]methanone

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

Combine 1-(3,4,5-trimethoxy-benzoyl)-3-phenyl-3-(2-methanesulfonyl-ethyl)-pyrrolidine (0.60 g, 1.30 mmol) and 4-[1-(4-fluoro-benzyl)-1 H-benzoimidazole-2-carbonyl]-piperidine (0.66 g, 1.95 mmol), and diisopropylethylamine (0.453 mL, 2.60 mmol) in chlorobenzene (8 mL). Heat to reflux. After 18 hours, partition the residue between ethyl acetate and water. Extract the organic layer 3 times with water and 1 time with saturated sodium chloride solution. Dry the organic layer over Na2So4, filter, and concentrate in vacuo to obtain a residue. Chromatograph the residue on silica gel eluting with 10/1/0.1 ethyl acetate/methanol/concentrated aqueous ammonium hydroxide to give the title compound: Rf=0.15 (silica gel, 10/1/0.1 ethyl acetate/methanol/concentrated aqueous ammonium hydroxide).

Workup

  1. temperatureHeat to reflux
  2. custompartition the residue between ethyl acetate and water
  3. extractionExtract the organic layer 3 times with water and 1 time with saturated sodium chloride solution
  4. customDry the organic layer over Na2So4
  5. filtrationfilter
  6. concentrationconcentrate in vacuo
  7. customto obtain a residue

Sources & evidence

ORD record
ord-b05ea48af79e41b6b142dc9ee3a03b33
Source dataset
uspto-grants-2001_12
Patent number
US06329392B1

Reaction notes

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