Triethylamine → 1-(3,4,5-trimethoxybenzyl)-3-(3-(4-(1-(3-carboethoxypropyl)-1H-benzimidazol-2-yl-amino)piperidin-1-yl)propyl)-3-(4-fluorophenylmethyl)-2-oxopyrrolidine

HRID 323505Notes

Reaction equation

HRID 323505 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:29]=[C:30]([O:34][CH3:35])[C:31]=1[O:32][CH3:33])[CH2:6][N:7]1[CH2:11][CH2:10][C:9]([CH2:20][C:21]2[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=2)([CH2:12][CH2:13][CH2:14]OS(C)(=O)=O)[C:8]1=[O:28].C(N(CC)CC)C.I.[C:44]([CH2:49][CH2:50][CH2:51][N:52]1[C:56]2[CH:57]=[CH:58][CH:59]=[CH:60][C:55]=2[N:54]=[C:53]1[NH:61][CH:62]1[CH2:67][CH2:66][NH:65][CH2:64][CH2:63]1)([O:46][CH2:47][CH3:48])=[O:45]>C(#N)C.ClCCl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:29]=[C:30]([O:34][CH3:35])[C:31]=1[O:32][CH3:33])[CH2:6][N:7]1[CH2:11][CH2:10][C:9]([CH2:12][CH2:13][CH2:14][N:65]2[CH2:66][CH2:67][CH:62]([NH:61][C:53]3[N:52]([CH2:51][CH2:50][CH2:49][C:44]([O:46][CH2:47][CH3:48])=[O:45])[C:56]4[CH:57]=[CH:58][CH:59]=[CH:60][C:55]=4[N:54]=3)[CH2:63][CH2:64]2)([CH2:20][C:21]2[CH:22]=[CH:23][C:24]([F:27])=[CH:25][CH:26]=2)[C:8]1=[O:28]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 184644831-(3,4,5-Trimethoxybenzyl)-3-(4-fluorophenylmethyl)-3-(3-methanesulfonyloxypropyl)-2-oxopyrrolidineHCID 86756600(1-(3-carboethoxypropyl)-1H-benzimidazol-2-yl)(piperidin-4-yl)amine hydriodic acid salt

Product 1

HCID 99184321-(3,4,5-trimethoxybenzyl)-3-(3-(4-(1-(3-carboethoxypropyl)-1H-benzimidazol-2-yl-amino)piperidin-1-yl)propyl)-3-(4-fluorophenylmethyl)-2-oxopyrrolidine

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
80 °C

Procedure

Combine 1-(3,4,5-trimethoxybenzyl)-3-(4-fluorophenylmethyl)-3-(3-methanesulfonyloxypropyl)-2-oxopyrrolidine (0.37 g, 0.73 mmol), triethylamine (0.45 mL, 3.23 mmol), and (1-(3-carboethoxypropyl)-1H-benzimidazol-2-yl)(piperidin-4-yl)amine hydriodic acid salt (0.40 g, 0.68 mmol) in acetonitrile (10 mL). Heat at 80° C. After 18 hours, cool, dilute the reaction mixture with dichloromethane and extract with brine. Dry the organic layer over MgSO4, filter, and evaporate in vacuo to give a residue. Chromatograph the residue on silica gel eluting with dichloromethane/methanol/concentrate aqueous ammonium hydroxide 95/5/0.05 to give the title compound: Rf=0.65 (silica gel, dichloromethane/methanol/concentrate aqueous ammonium hydroxide 95/5/0.1).

Workup

  1. temperaturecool
  2. extractionextract with brine
  3. dry with materialDry the organic layer over MgSO4
  4. filtrationfilter
  5. customevaporate in vacuo
  6. customto give a residue
  7. concentrationChromatograph the residue on silica gel eluting with dichloromethane/methanol/concentrate aqueous ammonium hydroxide 95/5/0.05

Sources & evidence

ORD record
ord-1bdc235a05e94503bf33dc1a7dbf06de
Source dataset
uspto-grants-2001_04
Patent number
US06211199B1

Reaction notes

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