Cesium carbonate → 2-(1-(6-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)-2-methylpyrimidin-4-yl)azetidin-3-yl)-1-methyl-1H-benzo[d]imidazole

HRID 2202819Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2202819
Cl[C:2]1[CH:7]=[C:6]([N:8]2[C:12]([CH3:13])=[N:11][C:10]([CH3:14])=[N:9]2)[N:5]=[C:4]([CH3:15])[N:3]=1.[NH:16]1[CH2:19][CH:18]([C:20]2[N:24]([CH3:25])[C:23]3[CH:26]=[CH:27][CH:28]=[CH:29][C:22]=3[N:21]=2)[CH2:17]1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[CH3:14][C:10]1[N:11]=[C:12]([CH3:13])[N:8]([C:6]2[N:5]=[C:4]([CH3:15])[N:3]=[C:2]([N:16]3[CH2:19][CH:18]([C:20]4[N:24]([CH3:25])[C:23]5[CH:26]=[CH:27][CH:28]=[CH:29][C:22]=5[N:21]=4)[CH2:17]3)[CH:7]=2)[N:9]=1

Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 624817454-chloro-6-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)-2-methylpyrimidineHCID 894881762-(azetidin-3-yl)-1-methyl-1H-1,3-benzodiazole

Produkt 1

HCID 715508042-(1-(6-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)-2-methylpyrimidin-4-yl)azetidin-3-yl)-1-methyl-1H-benzo[d]imidazoleAusbeute 78 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

Intermediate 2 (0.15 g, 0.67 mmol), Intermediate 1 (0.13 g, 0.67 mmol), and Cs2CO3 (0.66 g, 2.01 mmol) were suspended in DMF (6.7 mL) in a microwave vial. The vial was then capped and heated in the microwave at 100° C. for 30 min. After cooling to room temperature, the reaction was filtered and the filtrate was purified by reverse phase chromatography (acetonitrile/water/0.1% TFA). The fractions containing the product were partitioned between EtOAc and saturated NaHCO3. The organic layer was washed with brine, dried over Na2SO4 and concentrated to provide Example 1 (0.17 g, 78%) as a white solid. 1H NMR: (500 MHz, CD3OD) δ 7.63 (d, J=8 Hz, 1H), 7.5 (d, J=8 Hz, 1H), 7.28 (m, 2H), 6.66 (s, 1H), 4.66 (m, 2H), 4.53 (m, 3H), 3.83 (s, 3H), 2.84 (s, 3H), 2.51 (s, 3H), 2.36 (s, 3H). MS: m/z=375.4 (M+H).

Aufarbeitung

  1. customThe vial was then capped
  2. temperatureAfter cooling to room temperature
  3. filtrationthe reaction was filtered
  4. customthe filtrate was purified by reverse phase chromatography (acetonitrile/water/0.1% TFA)
  5. additionThe fractions containing the product
  6. customwere partitioned between EtOAc and saturated NaHCO3
  7. washThe organic layer was washed with brine
  8. dry with materialdried over Na2SO4
  9. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-7d7907bc92004eb39c43b875041a2121
Quelldatensatz
uspto-grants-2016_06
Patentnummer
US09365562B2

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