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

Cesium carbonate → Methyl 6-(5-methoxypyrazin-2-ylamino)-4-(8-methyl-8-azabicyclo[3.2.1]octan-3-ylamino)nicotinate

HRID 384649
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 384649
Cl[C:2]1[CH:11]=[C:10]([NH:12][CH:13]2[CH2:19][CH:18]3[N:20]([CH3:21])[CH:15]([CH2:16][CH2:17]3)[CH2:14]2)[C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][N:3]=1.[CH3:22][O:23][C:24]1[N:25]=[CH:26][C:27]([NH2:30])=[N:28][CH:29]=1.C(=O)([O-])[O-].[Cs+].[Cs+].C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=CC=1>>[CH3:22][O:23][C:24]1[N:25]=[CH:26][C:27]([NH:30][C:2]2[CH:11]=[C:10]([NH:12][CH:13]3[CH2:19][CH:18]4[N:20]([CH3:21])[CH:15]([CH2:16][CH2:17]4)[CH2:14]3)[C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][N:3]=2)=[N:28][CH:29]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 4

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 145364295-Methoxypyrazin-2-amineHCID 59613550Methyl 6-chloro-4-(8-methyl-8-azabicyclo[3.2.1]octan-3-ylamino)nicotinate

Produkt 1

HCID 42610356Methyl 6-(5-methoxypyrazin-2-ylamino)-4-(8-methyl-8-azabicyclo[3.2.1]octan-3-ylamino)nicotinate
Ausbeute 15 %

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

Methyl 6-chloro-4-(8-methyl-8-azabicyclo[3.2.1]octan-3-ylamino)nicotinate (26 mg, 0.084 mmol, prepared as described in Synthesis 62 and 63), 5-methoxypyrazin-2-amine (16 mg, 0.127 mmol), cesium carbonate (55 mg, 0.169 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (3.9 mg, 7 mol %), and tris(dibenzylideneacetone)dipalladium chloroform complex (3.5 mg, 3.5 mol %) were added to a vial which was flushed with nitrogen and sealed. Anhydrous toluene (0.3 mL) and DMF (0.1 mL) were added and nitrogen was bubbled through the stirred solution for 10 minutes. The mixture was heated by microwave irradiation at 130° C. for 30 minutes. The cooled solution was diluted with methanol and adsorbed onto an Isolute SCX-II column. The column was washed with methanol, then with 2M ammonia in methanol. The basic fractions concentrated. Preparative TLC, eluting with ethyl acetate-methanol-concentrated ammonia 10:1:0.2, gave methyl 6-(5-methoxypyrazin-2-ylamino)-4-(8-methyl-8-azabicyclo[3.2.1]octan-3-ylamino)nicotinate (5 mg, 15%) as an oil.

Aufarbeitung

  1. customwas flushed with nitrogen
  2. customsealed
  3. additionAnhydrous toluene (0.3 mL) and DMF (0.1 mL) were added
  4. customnitrogen was bubbled through the stirred solution for 10 minutes
  5. additionThe cooled solution was diluted with methanol
  6. washThe column was washed with methanol
  7. concentrationThe basic fractions concentrated
  8. washPreparative TLC, eluting with ethyl acetate-methanol-concentrated ammonia 10:1:0.2

Quellen und Nachweise

ORD-Eintrag
ord-0a95e6cfaf484ac2a7ce3b3fc3d69a33
Quelldatensatz
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08367658B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion