Nitrogen mustard hydrochloride → HCID 178480776, Verbindung

HRID 132051

Reaktionsgleichung

Reaktionsgleichung von HRID 132051
Cl.Cl[CH2:3][CH2:4][N:5]([CH2:7][CH2:8]Cl)[CH3:6].[F:10][C:11]1[CH:16]=[CH:15][C:14]([NH:17][C:18]([C:20]2[C:24]([NH2:25])=[CH:23][NH:22][N:21]=2)=[O:19])=[CH:13][CH:12]=1.C(N(C(C)C)CC)(C)C>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C=O)C>[F:10][C:11]1[CH:12]=[CH:13][C:14]([NH:17][C:18]([C:20]2[C:24]([N:25]3[CH2:8][CH2:7][N:5]([CH3:6])[CH2:4][CH2:3]3)=[CH:23][NH:22][N:21]=2)=[O:19])=[CH:15][CH:16]=1

Komponenten

6

Edukt 3

HCID 5935Nitrogen mustard hydrochlorideHCID 81531DiisopropylethylamineHCID 178508056HCID 178508056, Verbindung

Produkt 1

HCID 178480776HCID 178480776, VerbindungAusbeute 19,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 67553Tetrabutylammonium IodideKatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
200 °C

Versuchsvorschrift

Bis(2-chloroethyl)methylamine hydrochloride (97 mg; 0.5 mmol) was added to a stirred solution of 4-amino-1H-pyrazole-3-carboxylic acid (4-fluoro-phenyl)-amide (100 mg; 0.45 mmol), tetrabutylammonium iodide (20 mg; 0.045 mmol) and diisopropyethylamine (200 ul) 1.13 mmol) in DMF (5 ml), and the resulting mixture was heated at 200° C. (100 W) for 30 minutes in a CEM Discover™ microwave synthesiser. The DMF was removed under vacuum, then purified by flash column chromatography, eluting with dichloromethane/methanol/acetic acid/water (90:18:3:2). Product containing fractions were combined and evaporated, treated with HCl in ethyl acetate and then re-evaporated with toluene (2×20 ml) to give an off white solid (27 mg). (LC/MS: Rt 1.64, [M+H]+378).

Aufarbeitung

  1. customThe DMF was removed under vacuum
  2. custompurified by flash column chromatography
  3. washeluting with dichloromethane/methanol/acetic acid/water (90:18:3:2)
  4. additionProduct containing fractions
  5. customevaporated
  6. additiontreated with HCl in ethyl acetate
  7. customre-evaporated with toluene (2×20 ml)

Quellen und Nachweise

ORD-Eintrag
ord-23ac68d66eeb4bbe9731a53c9caa4c1e
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07385059B2

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