Diisopropylethylamine → N'-{2-[5-(4-Bromo-phenyl)-1H-imidazol-2-yl]-pyrrolidine-1-carbonyl}-N'-isopropyl-hydrazine-carboxylic acid methyl ester

HRID 2039165Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2039165
ClC(Cl)(O[C:5](=[O:11])OC(Cl)(Cl)Cl)Cl.[CH3:13][O:14][C:15]([NH:17][NH:18][CH:19]([CH3:21])[CH3:20])=[O:16].CCN(C(C)C)C(C)C.[Br:31][C:32]1[CH:37]=[CH:36][C:35]([C:38]2[NH:42][C:41]([CH:43]3[CH2:47][CH2:46][CH2:45][NH:44]3)=[N:40][CH:39]=2)=[CH:34][CH:33]=1>C(Cl)Cl>[CH3:13][O:14][C:15]([NH:17][N:18]([C:5]([N:44]1[CH2:45][CH2:46][CH2:47][CH:43]1[C:41]1[NH:42][C:38]([C:35]2[CH:36]=[CH:37][C:32]([Br:31])=[CH:33][CH:34]=2)=[CH:39][N:40]=1)=[O:11])[CH:19]([CH3:21])[CH3:20])=[O:16]

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 94429Triphosgene2×HCID 436506945-(4-Bromo-phenyl)-2-pyrrolidin-2-yl-1H-imidazoleHCID 57863323Methyl 2-isopropylhydrazinecarboxylate

Produkt 1

HCID 66621058N'-{2-[5-(4-Bromo-phenyl)-1H-imidazol-2-yl]-pyrrolidine-1-carbonyl}-N'-isopropyl-hydrazine-carboxylic acid methyl esterAusbeute 33,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Triphosgene (1.05 g) was dissolved in DCM (17 mL) and stirred at 0° C. N′-Isopropyl-hydrazine-carboxylic acid methyl ester (1.00 g) and DIPEA (1.5 mL) were dissolved in DCM (25 mL), and mixture was added to triphosgene solution and stirred for 10 minutes. 5-(4-Bromo-phenyl)-2-pyrrolidin-2-yl-1H-imidazole (2.65 g) was added. Reaction was stirred at room temperature for 1 hour and extracted twice with water (10 mL), once with brine (10 mL), and evaporated under vacuum. The resulting oil was subjected to silica gel chromatography using a 40 g ISCO column and effluent of 0-100% ethyl acetate:hexanes. The fractions containing product were combined and the solvent was removed under vacuum, giving N′-{2-[5-(4-Bromo-phenyl)-1H-imidazol-2-yl]-pyrrolidine-1-carbonyl}-N′-isopropyl-hydrazine-carboxylic acid methyl ester (533 mg, 16%).

Aufarbeitung

  1. stirringstirred for 10 minutes
  2. customReaction
  3. stirringwas stirred at room temperature for 1 hour
  4. extractionextracted twice with water (10 mL), once with brine (10 mL)
  5. customevaporated under vacuum
  6. additionThe fractions containing product
  7. customthe solvent was removed under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-1f8a8a2855f74cd48d84cde69e8738db
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08575118B2

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