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Ammonium formate → HCID 117643826, Verbindung

HRID 2171281
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2171281
C([O-])=O.[NH4+].[C:5]([C:7]1[CH:8]=[C:9]([F:49])[C:10]([NH:21][CH:22]2[CH2:27][CH2:26][N:25](C(OCC3C=CC=CC=3)=O)[CH2:24][CH:23]2[N:38]2[C:46](=[O:47])[C:45]3[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=3)[C:39]2=[O:48])=[N:11][C:12]=1[NH:13][C:14]1[CH:15]=[N:16][CH:17]=[C:18]([CH3:20])[CH:19]=1)#[N:6]>[Pd].C(OCC)(=O)C.CO>[O:48]=[C:39]1[C:40]2[C:45](=[CH:44][CH:43]=[CH:42][CH:41]=2)[C:46](=[O:47])[N:38]1[CH:23]1[CH:22]([NH:21][C:10]2[C:9]([F:49])=[CH:8][C:7]([C:5]#[N:6])=[C:12]([NH:13][C:14]3[CH:15]=[N:16][CH:17]=[C:18]([CH3:20])[CH:19]=3)[N:11]=2)[CH2:27][CH2:26][NH:25][CH2:24]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 2723923Ammonium formate2×HCID 117643277HCID 117643277, Verbindung

Produkt 1

HCID 117643826HCID 117643826, VerbindungAusbeute 52,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysator2×HCID 21584119Ethylacetate methanolLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

Ammonium formate (6 mg) and 10% Pd/C (6 mg) were added to an ethyl acetate/MeOH (1 ml/1 ml) solution containing benzyl 4-((5-cyano-3-fluoro-6-((5-methylpyridin-3-yl)amino)pyridin-2-yl)amino)-3-(1,3-dioxoisoindolin-2-yl)piperidin-1-carboxylate (37 mg) obtained in the 1st step in a nitrogen atmosphere, followed by heating and stirring at 70° C. for 1 hour. Next, ammonium formate (30 mg) and 10% Pd/C (30 mg) were added to the solution, followed by heating and stirring at 70° C. for 1 hour. The reaction solution was cooled to room temperature and insoluble matter was removed by filtration through Celite. Filter cake was washed with ethyl acetate. The resulting filtrate was mixed with wash liquid. The obtained organic layers were washed with saturated saline and dried over anhydrous sodium sulfate. The solvent was distilled away under reduced pressure. A white solid of 6-((3-(1,3-dioxoisoindolin-2-yl)piperidin-4-yl)amino)-5-fluoro-2-((5-methylpyridin-3-yl)amino)nicotinonitrile (15 mg) was thus obtained.

Aufarbeitung

  1. customobtained in the 1st step in a nitrogen atmosphere
  2. temperatureby heating
  3. temperatureby heating
  4. stirringstirring at 70° C. for 1 hour
  5. temperatureThe reaction solution was cooled to room temperature
  6. custominsoluble matter was removed by filtration through Celite
  7. filtrationFilter cake
  8. washwas washed with ethyl acetate
  9. additionThe resulting filtrate was mixed
  10. washwith wash liquid
  11. washThe obtained organic layers were washed with saturated saline
  12. dry with materialdried over anhydrous sodium sulfate
  13. distillationThe solvent was distilled away under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-5f92f8e901c44d5080cd7aedef5ac329
Quelldatensatz
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09051310B2

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