Diisopropylethylamine → 2-(Quinazolin-4-ylaminomethyl)-piperidine-1-carboxylic acid tert butyl ester

HRID 18082

Reaktionsgleichung

Reaktionsgleichung von HRID 18082
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:14][NH2:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].ClN1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[N:20]=[CH:19]C1.[CH:27]([N:30](C(C)C)CC)(C)C>O1CCCC1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[CH2:14][NH:15][C:27]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[N:20]=[CH:19][N:30]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 1502020tert-Butyl (2S)-2-(aminomethyl)piperidine-1-carboxylateHCID 866260114-Chloroquinoxaline

Produkt 1

HCID 866266042-(Quinazolin-4-ylaminomethyl)-piperidine-1-carboxylic acid tert butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

(S)-2-Aminomethyl-piperidine-1-carboxylic acid tert-butyl ester (1.0 g), 4-chloroquinoxaline (0.768 g) and diisopropylethylamine (0.816 ml) were dissolved in tetrahydrofuran (75 ml) and heated to reflux for 6 hours under an atmosphere of argon. After cooling, the reaction solution was partitioned between ethyl acetate and water. The organic layer was washed with saturated sodium hydrogen carbonate solution, saturated brine, dried and evaporated. The residue was chromatographed over silica gel, eluting with a gradient of 50 to 100% ethyl acetate in hexane. The title compound was obtained as a white foam (1.44 g).

Aufarbeitung

  1. temperatureheated
  2. temperatureto reflux for 6 hours under an atmosphere of argon
  3. temperatureAfter cooling
  4. customthe reaction solution was partitioned between ethyl acetate and water
  5. washThe organic layer was washed with saturated sodium hydrogen carbonate solution, saturated brine
  6. customdried
  7. customevaporated
  8. customThe residue was chromatographed over silica gel
  9. washeluting with a gradient of 50 to 100% ethyl acetate in hexane

Quellen und Nachweise

ORD-Eintrag
ord-43773e5d2c34440ca5b5489610e464ec
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07741329B2

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