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Cesium carbonate → HCID 117643277, Verbindung

HRID 2171280
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2171280
[NH2:1][C:2]1(C)[CH:7]=C[CH:5]=[N:4][CH2:3]1.[C:9](=[O:12])([O-])[O-:10].[Cs+].[Cs+].C[C:16]1(C)[C:42]2[C:37](=[C:38](P(C3C=CC=CC=3)C3C=CC=CC=3)[CH:39]=[CH:40][CH:41]=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.Cl[C:58]1[N:63]=[C:62]([NH:64][CH:65]2[CH2:70][CH2:69][N:68](C(OCC3C=CC=CC=3)=O)[CH2:67][CH:66]2[N:81]2[C:89](=[O:90])[C:88]3[C:83](=[CH:84][CH:85]=[CH:86][CH:87]=3)[C:82]2=[O:91])[C:61]([F:92])=[CH:60][C:59]=1[C:93]#[N:94].O1[CH2:100][CH2:99]OCC1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:93]([C:59]1[CH:60]=[C:61]([F:92])[C:62]([NH:64][CH:65]2[CH2:70][CH2:69][N:68]([C:9]([O:10][CH2:16][C:42]3[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=3)=[O:12])[CH2:67][CH:66]2[N:81]2[C:82](=[O:91])[C:83]3[C:88](=[CH:87][CH:86]=[CH:85][CH:84]=3)[C:89]2=[O:90])=[N:63][C:58]=1[NH:1][C:2]1[CH:3]=[N:4][CH:5]=[C:99]([CH3:100])[CH:7]=1)#[N:94]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 5

HCID 10796Cesium carbonateHCID 312751,4-DioxaneHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 89174215HCID 89174215, VerbindungHCID 117643958HCID 117643958, Verbindung

Produkt 1

HCID 117643277
HCID 117643277, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysator

Versuchsvorschrift

3-Amino-3-methylpyridine (9 mg), cesium carbonate (45 mg), Pd2(dba)3 (10 mg), and Xantphos (12 mg) were added to a dioxane (3 ml) solution containing benzyl 4-((6-chloro-5-cyano-3-fluoropyridin-2-yl)amino)-3-(1,3-dioxoisoindolin-2-yl)piperidin-1-carboxylate (37 mg), followed by microwave irradiation (Initiator™, 160° C., 10 minutes, 2.45 GHz, 0-240 W). The obtained residue was filtered through Celite and filter cake was washed with ethyl acetate. Subsequently, the solvent was distilled away from the filtrate under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1 to 1:1). Yellow oily matter of 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 (28 mg) was thus obtained.

Aufarbeitung

  1. customfollowed by microwave irradiation (Initiator™, 160° C., 10 minutes, 2.45 GHz, 0-240 W)
  2. filtrationThe obtained residue was filtered through Celite
  3. filtrationfilter cake
  4. washwas washed with ethyl acetate
  5. distillationSubsequently, the solvent was distilled away from the filtrate under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1 to 1:1)

Quellen und Nachweise

ORD-Eintrag
ord-4492ee030fb946bfaf76680e36f1553c
Quelldatensatz
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09051310B2

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