Potassium Carbonate → HCID 15542881, compound

HRID 2269906Notes

Reaction equation

HRID 2269906 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:38]=[C:39]([O:43][CH3:44])[C:40]=1[O:41][CH3:42])[C:6]([N:8]1[CH2:12][CH2:11][C:10]([CH2:19][CH2:20][N:21]2[CH2:26][CH2:25][CH:24]([C:27]([C:29]3[NH:33][C:32]4[CH:34]=[CH:35][CH:36]=[CH:37][C:31]=4[N:30]=3)=[O:28])[CH2:23][CH2:22]2)([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:9]1)=[O:7].Cl.Cl[CH2:47][C:48]1[CH:49]=[N:50][CH:51]=[CH:52][CH:53]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:38]=[C:39]([O:43][CH3:44])[C:40]=1[O:41][CH3:42])[C:6]([N:8]1[CH2:12][CH2:11][C:10]([CH2:19][CH2:20][N:21]2[CH2:26][CH2:25][CH:24]([C:27]([C:29]3[N:30]([CH2:47][C:48]4[CH:49]=[N:50][CH:51]=[CH:52][CH:53]=4)[C:31]4[CH:37]=[CH:36][CH:35]=[CH:34][C:32]=4[N:33]=3)=[O:28])[CH2:23][CH2:22]2)([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:9]1)=[O:7]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 233943-(Chloromethyl)pyridine hydrochlorideHCID 101213901-(3,4,5-trimethoxy-benzoyl)-3-[2-[4-[1H-benzoimidazole-2-carbonyl]-piperidin-1-yl]-ethyl]-3-phenyl-pyrrolidine

Product 1

HCID 15542881HCID 15542881, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

Combine 1-(3,4,5-trimethoxy-benzoyl)-3-[2-[4-[1H-benzoimidazole-2-carbonyl]-piperidin-1-yl]-ethyl]-3-phenyl-pyrrolidine (710 mg, 1.19 mmol), 3-(chloromethyl)pyridine hydrochloride (794 mg, 4.84 mmol), potassium carbonate (1.337 g, 9.67 mmol) in acetone (21 mL) and water (7 mL). Stir and heat at reflux for 24 h. Allow reaction mixture to cool to room temperature, and remove the acetone under vacuum. Add ethyl acetate to the reaction mixture and separate the organic layer. Extract the organic layer with saturated aqueous NaCl solution, dry over anhydrous Na2SO4, filter and concentrate in vacuo. Chromatograph the residue on silica gel eluting with 30% methanol/ethyl acetate to give the title compound: Rf=0.16 (silica gel, 20% methanol/ethyl acetate)]. Elemental Analysis calculated for C41H44N5O5: C 71.59; H 6.59; N 10.18; Found: C 69.84; H 6.75; N 9.82.

Workup

  1. temperatureheat
  2. temperatureat reflux for 24 h
  3. customAllow reaction mixture
  4. customremove the acetone under vacuum
  5. customAdd ethyl acetate to the reaction mixture and separate the organic layer
  6. extractionExtract the organic layer with saturated aqueous NaCl solution
  7. dry with materialdry over anhydrous Na2SO4
  8. filtrationfilter
  9. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-f80ea466e11a44629f0be9d0486787b5
Source dataset
uspto-grants-2001_12
Patent number
US06329392B1

Reaction notes

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