StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

Diisopropylethylamine → HCID 86726715, Verbindung

HRID 1499481
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1499481
Cl[C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][N:5]=[C:4]2[N:13]([CH2:16][C:17]3[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=3)[N:14]=[CH:15][C:3]=12.[NH:25]1[CH2:30][CH2:29][CH2:28][C@H:27]([NH:31][C:32](=[O:38])[O:33][C:34]([CH3:37])([CH3:36])[CH3:35])[CH2:26]1.CCN(C(C)C)C(C)C>C(O)CCC>[C:34]([O:33][C:32]([NH:31][C@H:27]1[CH2:28][CH2:29][CH2:30][N:25]([C:2]2[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][N:5]=[C:4]3[N:13]([CH2:16][C:17]4[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=4)[N:14]=[CH:15][C:3]=23)[CH2:26]1)=[O:38])([CH3:37])([CH3:35])[CH3:36]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 1514171tert-butyl N-[(3S)-piperidin-3-yl]carbamateHCID 53665897Ethyl 4-chloro-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridine-5-carboxylate

Produkt 1

HCID 86726715HCID 86726715, VerbindungAusbeute 86,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 2631-Butanol
Lösungsmittel

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

A mixture of ethyl 4-chloro-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridine-5-carboxylate (1.5 g, 4.3 mmol), tert-butyl (3S)-piperidin-3-ylcarbamate (1.0 g, 5.0 mmol) and DIPEA (0.84 g, 6.5 mmol) in 1-butanol (10 mL) was heated to 140° C. for 14 h, then allowed to cool. The mixture was concentrated under reduced pressure, and the resulting residue was diluted with EtOAc and washed with aq. NaHCO3. The organic extract was washed with water and brine, dried and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel using CombiFlash® apparatus, eluting with 20-100% EtOAc in hexanes, to give the sub-title compound (1.9 g, 86%). LCMS calc. for C27H36N5O5 (M+H)+: m/z=510.3. Found: 510.2.

Aufarbeitung

  1. temperatureto cool
  2. concentrationThe mixture was concentrated under reduced pressure
  3. additionthe resulting residue was diluted with EtOAc
  4. washwashed with aq. NaHCO3
  5. extractionThe organic extract
  6. washwas washed with water and brine
  7. customdried
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by column chromatography on silica gel using CombiFlash® apparatus
  10. washeluting with 20-100% EtOAc in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-d6440e608d5f402f9e0181610cd447ee
Quelldatensatz
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09200004B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion