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Potassium Phosphate, Tribasic → 2-(2-(4-(7-(1-(oxetan-3-yl)-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl)-1H-pyrazol-1-yl)spiro[3.3]heptan-2-yl)acetonitrile

HRID 1853090
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1853090
Cl[C:2]1[N:7]=[C:6]([C:8]2[CH:9]=[N:10][N:11]([C:13]3([CH2:20][C:21]#[N:22])[CH2:16][C:15]4([CH2:19][CH2:18][CH2:17]4)[CH2:14]3)[CH:12]=2)[N:5]2[CH:23]=[CH:24][N:25]=[C:4]2[CH:3]=1.[O:26]1[CH2:29][CH:28]([N:30]2[CH:34]=[C:33](B3OC(C)(C)C(C)(C)O3)[CH:32]=[N:31]2)[CH2:27]1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.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]>[O:26]1[CH2:29][CH:28]([N:30]2[CH:34]=[C:33]([C:2]3[N:7]=[C:6]([C:8]4[CH:9]=[N:10][N:11]([C:13]5([CH2:20][C:21]#[N:22])[CH2:14][C:15]6([CH2:17][CH2:18][CH2:19]6)[CH2:16]5)[CH:12]=4)[N:5]4[CH:23]=[CH:24][N:25]=[C:4]4[CH:3]=3)[CH:32]=[N:31]2)[CH2:27]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 62657Potassium Phosphate, TribasicHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 67455169HCID 67455169, Verbindung2×HCID 866853442-(2-(4-(7-chloroimidazo[1,2-c]pyrimidin-5-yl)-1H-pyrazol-1-yl)spiro[3.3]heptan-2-yl)acetonitrile

Produkt 1

HCID 67457897
2-(2-(4-(7-(1-(oxetan-3-yl)-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl)-1H-pyrazol-1-yl)spiro[3.3]heptan-2-yl)acetonitrile
Ausbeute 74 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

2-(2-(4-(7-Chloroimidazo[1,2-c]pyrimidin-5-yl)-1H-pyrazol-1-yl)spiro[3.3]heptan-2-yl)acetonitrile (0.200 g, 0.567 mmol), 1-(oxetan-3-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (Table 2, compound f; 0.213 g, 0.850 mmol), dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine (0.054 g, 0.113 mmol) and K3PO4 (0.85 mL, 1.7 mmol) were suspended in 1,4-dioxane (10 mL) and purged with Ar (g). Pd2dba3 (0.052 g, 0.057 mmol) was added, and the system sealed and heated at 80° C. overnight. The reaction mixture was cooled to ambient temperature and partitioned between saturated aqueous NaHCO3 and EtOAc. The organic layer was washed with brine, dried (MgSO4), filtered and concentrated under reduced pressure to afford the crude material, which was purified by flash column chromatography, eluting with 2-3% (9:1 MeOH:NH4OH)/DCM to provide 2-(2-(4-(7-(1-(oxetan-3-yl)-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl)-1H-pyrazol-1-yl)spiro[3.3]heptan-2-yl)acetonitrile (0.184 g, 0.418 mmol, 74% yield). MS (apci) m/z=441.2 (M+H).

Aufarbeitung

  1. custompurged with Ar (g)
  2. customthe system sealed
  3. temperatureThe reaction mixture was cooled to ambient temperature
  4. custompartitioned between saturated aqueous NaHCO3 and EtOAc
  5. washThe organic layer was washed with brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customto afford the crude material, which
  10. customwas purified by flash column chromatography
  11. washeluting with 2-3% (9:1 MeOH:NH4OH)/DCM

Quellen und Nachweise

ORD-Eintrag
ord-0001426a4d65497098c728ce4cb39ce1
Quelldatensatz
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08962596B2

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