Iodoethane → 1-{4-[(1-ethyl-1H-benzo[d]imidazol-2-yl)methyl]benzoyl}pyrrolidin-3-yl methanesulfonate

HRID 1163088Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1163088
[CH3:1][S:2]([O:5][CH:6]1[CH2:10][CH2:9][N:8]([C:11](=[O:28])[C:12]2[CH:17]=[CH:16][C:15]([CH2:18][C:19]3[NH:23][C:22]4[CH:24]=[CH:25][CH:26]=[CH:27][C:21]=4[N:20]=3)=[CH:14][CH:13]=2)[CH2:7]1)(=[O:4])=[O:3].C(=O)([O-])[O-].[K+].[K+].[CH2:35](I)[CH3:36]>CN(C=O)C>[CH3:1][S:2]([O:5][CH:6]1[CH2:10][CH2:9][N:8]([C:11](=[O:28])[C:12]2[CH:17]=[CH:16][C:15]([CH2:18][C:19]3[N:20]([CH2:35][CH3:36])[C:21]4[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=4[N:23]=3)=[CH:14][CH:13]=2)[CH2:7]1)(=[O:4])=[O:3]

Komponenten

5

Edukt 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 866152161-(4-((1H-Benzo[d]imidazol-2-yl)methyl)benzoyl)pyrrolidin-3-yl Methanesulfonate

Produkt 1

HCID 866152171-{4-[(1-ethyl-1H-benzo[d]imidazol-2-yl)methyl]benzoyl}pyrrolidin-3-yl methanesulfonateAusbeute 19 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
-5 °C

Versuchsvorschrift

A stirred solution of 1-{4-[(1H-benzo[d]imidazol-2-yl)methyl]benzoyl}-pyrrolidin-3-yl methanesulfonate (0.250 g, 0.6 mmol) in DMF was treated with potassium carbonate (0.260 g, 1.9 mmol), cooled to −5° C., treated dropwise with ethyl iodide (0.24 g, 1.5 mmol) at 0° C. over 20 min, warmed to room temperature, heated at 50° C. for 3 h, cooled to room temperature and filtered. The filtrate was concentrated in vacuo. The resultant residue was dissolved in ethyl acetate, washed with water, dried over sodium sulfate and concentrated in vacuo. Purification of this residue by column chromatography (neutral alumina, chloroform:methanol 100:0→98:2) afforded 1-{4-[(1-ethyl-1H-benzo[d]imidazol-2-yl)methyl]benzoyl}pyrrolidin-3-yl methanesulfonate (19%). 1H NMR (400 MHz, CDCl3): 7.79-7.77 (m, 1H), 7.44-7.51 (m, 3H), 7.32-7.25 (m, 4H), 5.37 & 5.23 (bs, 1H), 4.36 (s, 2H), 4.05-4.10 (q, J=8 Hz, 2H), 3.93 (bs, 1H), 3.82 (m, 1H), 3.57-3.71 (bs, 2H), 3.08 & 3.00 (s, 3H), 2.33-2.36 (m, 1H), 2.17-2.21 (m, 1H), 1.18-1.22 (t, J=8 Hz, 3H). [M+H] 428.

Aufarbeitung

  1. temperaturewarmed to room temperature
  2. temperatureheated at 50° C. for 3 h
  3. temperaturecooled to room temperature
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated in vacuo
  6. dissolutionThe resultant residue was dissolved in ethyl acetate
  7. washwashed with water
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated in vacuo
  10. customPurification of this residue by column chromatography (neutral alumina, chloroform:methanol 100:0→98:2)

Quellen und Nachweise

ORD-Eintrag
ord-258b0575af254d32bd83840fe68e18e2
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07820825B2

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