2-Methoxyethylamine → 1-(2-methoxy-ethyl)-2,6-dimethyl-4-(3-methyl-1H-indazol-5-yl)-1,4-dihydro-pyridine-3,5-dicarbonitrile

HRID 218501

Reaktionsgleichung

Reaktionsgleichung von HRID 218501
[NH2:1]/[C:2](/[CH3:6])=[CH:3]\[C:4]#[N:5].[CH3:7][O:8][CH2:9][CH2:10]N.[CH3:12][C:13]1[C:21]2[C:16](=[CH:17][CH:18]=[C:19]([CH:22]=O)[CH:20]=2)[NH:15][N:14]=1>C(O)C>[CH3:7][O:8][CH2:9][CH2:10][N:1]1[C:2]([CH3:6])=[C:3]([C:4]#[N:5])[CH:22]([C:19]2[CH:20]=[C:21]3[C:16](=[CH:17][CH:18]=2)[NH:15][N:14]=[C:13]3[CH3:12])[C:3]([C:4]#[N:5])=[C:2]1[CH3:6]

Komponenten

5

Edukt 3

HCID 80182-MethoxyethylamineHCID 5325263(2Z)-3-Amino-2-butenenitrileHCID 178434286HCID 178434286, Verbindung

Produkt 1

HCID 1784957891-(2-methoxy-ethyl)-2,6-dimethyl-4-(3-methyl-1H-indazol-5-yl)-1,4-dihydro-pyridine-3,5-dicarbonitrileAusbeute 6,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

164.2 mg (2 mmols) 3-aminocrotononitrile and 150.2 mg (2 mmols) 2-methoxyethylamine were dissolved in 8 mL ethanol and refluxed under argon for 3 hours. The solvent was distilled off under vacuum and the residue dissolved in 10 mL acetic acid. 160.2 mg (1 mmol) 3-methyl-1H-indazole-5-carbaldehyde (from Synthetic Preparation 10) were added. The mixture was stirred for 3 hours at 100° C. and then concentrated under vacuum. Purification by column chromatography gave 1-(2-methoxy-ethyl)-2,6-dimethyl-4-(3-methyl-1H-indazol-5-yl)-1,4-dihydro-pyridine-3,5-dicarbonitrile (22 mg) (Cpd. No. 310). 1H-NMR (DMSO-d6): δ=12.68 (br s, 1H), 7.51 (s, 1H), 7.47 (d, 1H), 7.26 (d, 1H), 4.40 (s, 1H), 3.86 (t, 2H), 3.52 (t, 2H), 3.37 (s, 3H), 2.50 (s, 3H; covered by DMSO), 2.25 (s, 6H) ppm.

Aufarbeitung

  1. temperaturerefluxed under argon for 3 hours
  2. distillationThe solvent was distilled off under vacuum
  3. dissolutionthe residue dissolved in 10 mL acetic acid
  4. concentrationconcentrated under vacuum
  5. customPurification by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-a3db22863c6943cea65d2d4ba77c870e
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08198456B2

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