Potassium Acetate → 1-Methyl-5-(5-methyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazin-2-ylamino)-6-oxo-1,6-dihydropyridazin-3-ylboronic Acid

HRID 407801Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 407801
Cl[C:2]1[CH:3]=[C:4]([NH:10][C:11]2[CH:20]=[C:14]3[CH2:15][N:16]([CH3:19])[CH2:17][CH2:18][N:13]3[N:12]=2)[C:5](=[O:9])[N:6]([CH3:8])[N:7]=1.[B:21]1(B2OC(C)(C)C(C)(C)O2)[O:25]C(C)(C)C(C)(C)[O:22]1.CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.C([O-])(=O)C.[K+]>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].O1CCOCC1>[CH3:8][N:6]1[C:5](=[O:9])[C:4]([NH:10][C:11]2[CH:20]=[C:14]3[CH2:15][N:16]([CH3:19])[CH2:17][CH2:18][N:13]3[N:12]=2)=[CH:3][C:2]([B:21]([OH:25])[OH:22])=[N:7]1

Komponenten

7

Edukt 4

HCID 517044Potassium AcetateHCID 2733548Bis(pinacolato)diboraneHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 666346996-chloro-2-methyl-4-(5-methyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazin-2-ylamino)pyridazin-3(2H)-one

Produkt 1

HCID 866840631-Methyl-5-(5-methyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazin-2-ylamino)-6-oxo-1,6-dihydropyridazin-3-ylboronic Acid

Reagenzien, Katalysatoren, Lösungsmittel 2

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

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

A 50-mL round-bottomed flask equipped with a magnetic stirrer and a reflux condenser was charged with 153a (200 mg, 0.68 mmol), bis(pinacolato)diboron (Pin2B2, 863 mg, 3.40 mmol), Pd2(dba)3 (55 mg, 0.060 mmol), X-Phos (60 mg, 0.12 mmol), potassium acetate (60 mg, 1.36 mmol), and 1,4-dioxane (10 mL). The system was evacuated and then refilled with N2. It was then heated at 50° C. for 2 h. After completion of the reaction, the mixture was filtered and the solid was washed with ethyl acetate (10 mL). The combined filtrate was evaporated under reduced pressure to afford 153b as a pale yellow solid, which was used in the next step. MS-ESI: [M+H]+ 305.1.

Aufarbeitung

  1. customA 50-mL round-bottomed flask equipped with a magnetic stirrer and a reflux condenser
  2. customThe system was evacuated
  3. additionrefilled with N2
  4. customAfter completion of the reaction
  5. filtrationthe mixture was filtered
  6. washthe solid was washed with ethyl acetate (10 mL)
  7. customThe combined filtrate was evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-127c5a8ffa8b417489a50e1b2183b50a
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08754077B2

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