Triethylamine → HCID 86666961, Verbindung

HRID 571714Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 571714
[CH3:1][C@@H:2]1[CH2:7][NH:6][CH2:5][C@H:4]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:3]1.Cl[C:17]1[N:22]=[CH:21][N:20]=[C:19]2[N:23]([CH2:26][O:27][CH2:28][CH2:29][Si:30]([CH3:33])([CH3:32])[CH3:31])[N:24]=[CH:25][C:18]=12.CCN(CC)CC>CN(C=O)C.O>[CH3:1][C@@H:2]1[CH2:7][N:6]([C:17]2[N:22]=[CH:21][N:20]=[C:19]3[N:23]([CH2:26][O:27][CH2:28][CH2:29][Si:30]([CH3:33])([CH3:32])[CH3:31])[N:24]=[CH:25][C:18]=23)[CH2:5][C@H:4]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:3]1

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 57538111HCID 57538111, VerbindungHCID 58386822cis-3-(Boc-amino)-5-methylpiperidine

Produkt 1

HCID 86666961HCID 86666961, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of tert-butyl (3R,5S)-5-methylpiperidin-3-ylcarbamate (150 mg, 0.7 mmol), 4-chloro-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazolo[3,4-d]pyrimidine (200 mg, 0.7 mmol) and Et3N (195 μL, 1.4 mmol) in DMF (5 mL) was heated at 80° C. for 16 h. The solution was cooled, diluted with water, extracted with EtOAc, washed with aq. citric acid and aq. NaHCO3, dried (Na2SO4), filtered, and concentrated in vacuo to afford a residue, which was purified by column chromatography (silica gel, gradient EtOAc in hexanes).

Aufarbeitung

  1. temperatureThe solution was cooled
  2. extractionextracted with EtOAc
  3. washwashed with aq. citric acid and aq. NaHCO3
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto afford a residue, which
  8. customwas purified by column chromatography (silica gel, gradient EtOAc in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-6dbb325c95da44bb9b93831e42d743c1
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09029359B2

Notizen zur Reaktion

Wird geladen…