Iodoethane → 2-(1-(6-(3,5-Dimethyl-1H-1,2,4-triazol-1-yl)-2-methylpyrimidin-4-yl)azetidin-3-yl)-1-ethyl-1H-benzo[d]imidazole

HRID 2202828Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2202828
[CH3:1][C:2]1[N:6]=[C:5]([CH3:7])[N:4]([C:8]2[N:13]=[C:12]([CH3:14])[N:11]=[C:10]([N:15]3[CH2:18][CH:17]([C:19]4[NH:23][C:22]5[CH:24]=[CH:25][CH:26]=[CH:27][C:21]=5[N:20]=4)[CH2:16]3)[CH:9]=2)[N:3]=1.[CH2:28](I)[CH3:29].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[CH3:1][C:2]1[N:6]=[C:5]([CH3:7])[N:4]([C:8]2[N:13]=[C:12]([CH3:14])[N:11]=[C:10]([N:15]3[CH2:18][CH:17]([C:19]4[N:23]([CH2:28][CH3:29])[C:22]5[CH:24]=[CH:25][CH:26]=[CH:27][C:21]=5[N:20]=4)[CH2:16]3)[CH:9]=2)[N:3]=1

Komponenten

5

Edukt 3

HCID 6340IodoethaneHCID 10796Cesium carbonateHCID 715503742-(1-(6-(3,5-Dimethyl-1H-1,2,4-triazol-1-yl)-2-methylpyrimidin-4-yl)azetidin-3-yl)-1H-benzo[d]imidazole

Produkt 1

HCID 715505172-(1-(6-(3,5-Dimethyl-1H-1,2,4-triazol-1-yl)-2-methylpyrimidin-4-yl)azetidin-3-yl)-1-ethyl-1H-benzo[d]imidazole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

Example 107 (13 mg, 0.036 mmol), ethyl iodide (5.6 mg, 0.036 mmol), and cesium carbonate (58 mg, 0.18 mmol) were combined in degassed DMF (1 mL) and heated at 60° C. for 30 min. The mixture was cooled to room temperature, filtered and purified by reverse phase HPLC, providing Example 114 as a solid. 1H NMR: (400 MHz, d6-DMSO) δ 7.71-7.67 (m, 2H), 7.37-7.30 (m, 2H) 6.56 (s, 1H), 4.62-4.58 (m, 3H), 4.47-4.44 (m, 2H), 4.30 (q, J=7.2 Hz, 2H), 2.77 (s, 3H), 2.45 (s, 3H), 2.29 (s, 3H), 1.34 (t, J=7.1 Hz, 3H) ppm; MS: m/z=389.4 (M+H).

Aufarbeitung

  1. temperatureThe mixture was cooled to room temperature
  2. filtrationfiltered
  3. custompurified by reverse phase HPLC

Quellen und Nachweise

ORD-Eintrag
ord-267a359c969240b783ddd6389fcacc5a
Quelldatensatz
uspto-grants-2016_06
Patentnummer
US09365562B2

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