(2-Chloroethyl)dimethylamine, chloride → HCID 178483838, Verbindung

HRID 2118247

Reaktionsgleichung

Reaktionsgleichung von HRID 2118247
[CH:1]1([NH:4][C:5]([C@H:7]2[CH2:12][CH2:11][C@H:10]([CH2:13][N:14]([C:16]3[N:21]=[CH:20][C:19]([Br:22])=[CH:18][N:17]=3)[CH3:15])[CH2:9][CH2:8]2)=[O:6])[CH2:3][CH2:2]1.[H-].[Na+].[Cl-].Cl[CH2:27][CH2:28][NH+:29]([CH3:31])[CH3:30]>CC(N(C)C)=O>[CH:1]1([N:4]([CH2:27][CH2:28][N:29]([CH3:31])[CH3:30])[C:5]([C@H:7]2[CH2:8][CH2:9][C@H:10]([CH2:13][N:14]([C:16]3[N:21]=[CH:20][C:19]([Br:22])=[CH:18][N:17]=3)[CH3:15])[CH2:11][CH2:12]2)=[O:6])[CH2:3][CH2:2]1

Komponenten

5

Edukt 3

HCID 20717(2-Chloroethyl)dimethylamine, chlorideHCID 24758Sodium hydrideHCID 178484067HCID 178484067, Verbindung

Produkt 1

HCID 178483838HCID 178483838, VerbindungAusbeute 68 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 31374DimethylacetamideLösungsmittel

Versuchsvorschrift

0.12 g (0.33 mmol) of trans-4-{[(5-bromo-pyrimidin-2-yl)-methyl-amino]-methyl}-cyclohexanecarboxylic acid cyclopropylamide was dissolved in 10 mL of DMA and treated with 0.21 g (4.90 mmol, 14 eq) of NaH (55% in oil) at 0° C. then warmed to RT. The mixture was then treated with 0.47 g (3.27 mmol, 10 eq) of N-(2-chlorethyl)-N,N-dimethylammonium chloride at 0° C. and warmed to RT. The reaction was stirred for 27 h, then partitioned between Et2O (×3)/aqueous 10% NaHCO3, washed once with aqueous 10% NaCl, dried over Na2SO4 and evaporated. The residue was chromatographed on silica gel (20g) with CH2Cl2:MeOH 95:5 to yield 0.09 g (68% over 2 steps) of pure trans-4-{[(5-bromo-pyrimidin-2-yl)-methyl-amino]-methyl}-cyclohexanecarboxylic acid cyclopropyl-(2-dimethylamino-ethyl)-amide, MS: 438 (MH+, 1Br).

Aufarbeitung

  1. temperaturewarmed to RT
  2. custompartitioned between Et2O (×3)/aqueous 10% NaHCO3
  3. washwashed once with aqueous 10% NaCl
  4. dry with materialdried over Na2SO4
  5. customevaporated
  6. customThe residue was chromatographed on silica gel (20g) with CH2Cl2:MeOH 95:5

Quellen und Nachweise

ORD-Eintrag
ord-2370d902e4b34de3a1291d086a11dc14
Quelldatensatz
uspto-grants-2008_10
Patentnummer
US07442791B2

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