2-Dimethylaminopyridine → 1-[(5-Chlorothien-2-yl)sulfonyl]-3-[2-(dimethylamino)ethyl]-1,3-dihydro-2H-benzimidazol-2-one

HRID 1984537Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1984537
[CH3:1][N:2]([CH3:15])[CH2:3][CH2:4][N:5]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[NH:7][C:6]1=[O:14].[Cl:16][C:17]1[S:21][C:20]([S:22](Cl)(=[O:24])=[O:23])=[CH:19][CH:18]=1.C(N(C(C)C)CC)(C)C.CN(C1C=CC=CN=1)C>C1COCC1>[Cl:16][C:17]1[S:21][C:20]([S:22]([N:7]2[C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[N:5]([CH2:4][CH2:3][N:2]([CH3:15])[CH3:1])[C:6]2=[O:14])(=[O:24])=[O:23])=[CH:19][CH:18]=1

Komponenten

6

Edukt 4

HCID 218852-DimethylaminopyridineHCID 81531DiisopropylethylamineHCID 27339255-Chlorothiophene-2-sulfonyl chlorideHCID 148946781-[2-(Dimethylamino)ethyl]-1,3-dihydrobenzimidazol-2-one

Produkt 1

HCID 114290941-[(5-Chlorothien-2-yl)sulfonyl]-3-[2-(dimethylamino)ethyl]-1,3-dihydro-2H-benzimidazol-2-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 1-[2-(dimethylamino)ethyl]-1,3-dihydrobenzimidazol-2-one (20 mg, 0.1 mmol) in THF at room temperature is treated with (5-chlorothien-2-yl)sulfonyl chloride (26 mg, 0.12 mmol) followed by diisopropylethylamine (25 uL, 0.2 mmol) and dimethylaminopyridine (5 mg), stirred at room temperature for 16 hours and concentrated in vacuo. The resultant residue is dissolved in a mixture of dimethylsulfoxide, methanol and water and purified by Gilson1 preparative HPLC to give the title product, 16 mg, [M+H] 386, retention time (RT) 2.83 minutes. 1Gilson Preparative HPLC conditions: Gilson Preparative HPLC system; YMC Pro C18, 20 mm×50 mm ID, 5 uM column; 2 mL injection; Solvent A: 0.02% TFA/water; Solvent B:0.02% TFA/acetonitrile; Gradient: Time 0: 95% A; 2 min: 95% A; 14 min: 10% A, 15 min: 10% A, 16 min: 95% A; Flow rate 22.5 mL/min; Detection: 254 nm DAD.

Aufarbeitung

  1. concentrationconcentrated in vacuo
  2. dissolutionThe resultant residue is dissolved in a mixture of dimethylsulfoxide, methanol and water
  3. custompurified by Gilson1 preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-b202429ebe3943e18864e1e2ed012ecb
Quelldatensatz
uspto-grants-2009_06
Patentnummer
US07544701B2

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