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Triethylamine → N-[3-(3-chloro-5-cyano-2-methyl-1H-pyrrol-1-yl)-1-methylpropyl]-2-cyano-3,4,4-trimethylpentanamide

HRID 720776
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 720776
[C:1]([CH:3]([CH:7]([CH3:12])[C:8]([CH3:11])([CH3:10])[CH3:9])[C:4]([OH:6])=O)#[N:2].[NH2:13][CH:14]([CH3:26])[CH2:15][CH2:16][N:17]1[C:21]([CH3:22])=[C:20]([Cl:23])[CH:19]=[C:18]1[C:24]#[N:25].C(N(CC)CC)C>S(Cl)(Cl)=O.C(OCC)(=O)C>[Cl:23][C:20]1[CH:19]=[C:18]([C:24]#[N:25])[N:17]([CH2:16][CH2:15][CH:14]([NH:13][C:4](=[O:6])[CH:3]([C:1]#[N:2])[CH:7]([CH3:12])[C:8]([CH3:11])([CH3:10])[CH3:9])[CH3:26])[C:21]=1[CH3:22]
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Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 218952532-Cyano-3,4,4-trimethylpentanoic acidHCID 218952681-(3-aminobutyl)-4-chloro-5-methyl-1H-pyrrole-2-carbonitrile

Produkt 1

HCID 21895244N-[3-(3-chloro-5-cyano-2-methyl-1H-pyrrol-1-yl)-1-methylpropyl]-2-cyano-3,4,4-trimethylpentanamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8857Ethyl Acetate
Lösungsmittel
HCID 24386Thionyl ChlorideLösungsmittel2×

Versuchsvorschrift

A solution of 0.54 g (3.5 mmol) 2-cyano-3,4,4-trimethylpentanoic acid in 15 mL thionyl chloride was heated at reflux for 30 min. The thionyl chloride was stripped and the residue was dried in vacuo. The residue was then dissolved in 20 mL methylene chloride and a solution of 0.66 g (3.13 mmol) of 1-(3-aminobutyl)-4-chloro-5-methyl-1H-pyrrole-2-carbonitrile and 0.59 mL (4.2 mmol) triethylamine was added dropwise. The mixture was stirred at room temperature overnight. Solvent was stripped and the residue was taken up in ethyl acetate which was washed with water and brine. Drying (MgSO4) and removal of solvent gave an oil which was chromatographed (40% ether in hexanes) on silica gel to give the title compound as a mixture of diastereomers, mp 111–118° C. 1H NMR (CDCl3) δ 1.0 (m, 3H), 1.2–1.3 (2m, 6H), 1.4 (d, 1H), 1.6 (m, 2H), 1.9 (m, 2H), 2.2 (m, 3H), 4.1 (2m, 2H), 5.7 (m, 1H), 6.65 (2s, 1H).

Aufarbeitung

  1. temperatureat reflux for 30 min
  2. customthe residue was dried in vacuo
  3. dissolutionThe residue was then dissolved in 20 mL methylene chloride
  4. washwas washed with water and brine
  5. customDrying
  6. custom(MgSO4) and removal of solvent
  7. customgave an oil which
  8. customwas chromatographed (40% ether in hexanes) on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-ff5eaa747ed84a6ab5ad0e08fe7251bb
Quelldatensatz
uspto-grants-2006_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07135585B2

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