Diisopropylamine → HCID 66823106, Verbindung

HRID 331711

Reaktionsgleichung

Reaktionsgleichung von HRID 331711
[CH2:1]([C:8]1([C:12]2[CH:13]=[C:14]([CH:28]=[CH:29][CH:30]=2)[O:15][CH2:16][CH2:17][NH:18][S:19]([C:22]2[N:23]=[CH:24][N:25]([CH3:27])[CH:26]=2)(=[O:21])=[O:20])[CH2:11][NH:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(NC(C)C)(C)C.[F:38][CH2:39][C:40](Cl)=[O:41]>ClCCl>[CH2:1]([C:8]1([C:12]2[CH:13]=[C:14]([CH:28]=[CH:29][CH:30]=2)[O:15][CH2:16][CH2:17][NH:18][S:19]([C:22]2[N:23]=[CH:24][N:25]([CH3:27])[CH:26]=2)(=[O:21])=[O:20])[CH2:11][N:10]([C:40](=[O:41])[CH2:39][F:38])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 7912DiisopropylamineHCID 9663Fluoroacetyl chlorideHCID 56835964N-(2-(3-(3-benzylazetidin-3-yl)phenoxy)ethyl)-1-methyl-1H-imidazole-4-sulfonamide

Produkt 1

HCID 66823106HCID 66823106, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a stirred solution of N-(2-(3-(3-benzylazetidin-3-yl)phenoxy)ethyl)-1-methyl-1H-imidazole-4-sulfonamide (81 mg, 0.190 mmol) in dry dichloromethane (1.5 ml) containing diisopropylamine (0.066 ml, 0.380 mmol) under argon was added fluoroacetyl chloride (0.022 ml, 0.285 mmol) and stirred at room temperature for 1 h. Washed with 1N HCl, sodium bicarbonate and brine, dried over MgSO4, filtered, evaporated and the crude material was purified by flash silica gel chromatography on 4 g SiO2-cartridge using 5% MeOH in dichloromethane affording 68.7 mg of a white solid.

Aufarbeitung

  1. washWashed with 1N HCl, sodium bicarbonate and brine
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. customevaporated
  5. customthe crude material was purified by flash silica gel chromatography on 4 g SiO2-cartridge

Quellen und Nachweise

ORD-Eintrag
ord-3b2cfca9b6ed46d0b22b4c8e6580ad46
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08877794B2

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