Diisopropylethylamine → HCID 58622896, Verbindung

HRID 1269628Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1269628
[CH2:1]([NH:5][CH2:6][C:7]1[CH:19]=[CH:18][C:10]([O:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:9]([CH3:20])[CH:8]=1)[CH2:2][CH2:3][CH3:4].C(N(CC)C(C)C)(C)C.[Cl:30][C:31]1[CH:36]=[CH:35][C:34]([C:37]2[CH:42]=[CH:41][N:40]=[C:39](S(C)(=O)=O)[N:38]=2)=[CH:33][CH:32]=1>C(Cl)Cl>[CH2:1]([N:5]([CH2:6][C:7]1[CH:19]=[CH:18][C:10]([O:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:9]([CH3:20])[CH:8]=1)[C:39]1[N:38]=[C:37]([C:34]2[CH:35]=[CH:36][C:31]([Cl:30])=[CH:32][CH:33]=2)[CH:42]=[CH:41][N:40]=1)[CH2:2][CH2:3][CH3:4]

Komponenten

5

Edukt 3

HCID 81531Diisopropylethylamine2×HCID 219059934-(4-Chlorophenyl)-2-(methylsulfonyl)pyrimidineHCID 58622846Ethyl {4-[(butylamino)methyl]-2-methylphenoxy}acetate

Produkt 1

HCID 58622896HCID 58622896, VerbindungAusbeute 23,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a mixture of the ethyl {4-[(butylamino)methyl]-2-methylphenoxy}acetate (686 mg, 2.46 mmol) and N,N-diisopropylethylamine (285 μL, 1.64 mmol) was added 4-(4-chlorophenyl)-2-(methylsulfonyl)pyrimidine (439 mg, 1.64 mmol) and the resultant mixture heated at 100° C. for 16 h in a reactivial. The cooled reaction mixture were then treated with N,N-diisopropylethylamine (285 μL, 1.64 mmol) and heated for a further 16 h at 100° C. in the reactivial. The cooled reaction mixtures were diluted with CH2Cl2 (30 mL), washed with water (20 mL), the aqueous extracted with CH2Cl2 (30 mL), the CH2Cl2 extracts combined and the solvent removed in vacuo. Purification by Biotage™ chromatography (silica, 90 g) eluted with 10:1 cyclohexane:EtOAc gave the title compound as a colourless gum (178 mg).

Aufarbeitung

  1. customThe cooled reaction mixture
  2. customThe cooled reaction mixtures
  3. washwashed with water (20 mL)
  4. extractionthe aqueous extracted with CH2Cl2 (30 mL)
  5. customthe solvent removed in vacuo
  6. customPurification by Biotage™ chromatography (silica, 90 g)
  7. washeluted with 10:1 cyclohexane

Quellen und Nachweise

ORD-Eintrag
ord-c68e20e8a43c4af8b660d33bd1a340f8
Quelldatensatz
uspto-grants-2007_04
Patentnummer
US07199239B2

Notizen zur Reaktion

Wird geladen…