Dimethyl Sulfoxide → HCID 59427282, Verbindung

HRID 1042821Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1042821
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]#[N:13])=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1.[CH2:14]([C:16]1[CH:21]=[C:20]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[N:19]=[N:18][C:17]=1[NH:28][C:29]1[CH:34]=[CH:33][C:32]([OH:35])=[CH:31][CH:30]=1)[CH3:15].C(=O)([O-])[O-:37].[Cs+].[Cs+].CS(C)=O>O>[CH2:14]([C:16]1[CH:21]=[C:20]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[N:19]=[N:18][C:17]=1[NH:28][C:29]1[CH:30]=[CH:31][C:32]([O:35][C:2]2[C:11]3[C:6](=[CH:7][C:8]([C:12]([NH2:13])=[O:37])=[CH:9][CH:10]=3)[N:5]=[CH:4][CH:3]=2)=[CH:33][CH:34]=1)[CH3:15]

Komponenten

6

Edukt 4

HCID 679Dimethyl SulfoxideHCID 10796Cesium carbonateHCID 220545814-Chloroquinoline-7-carbonitrileHCID 136131615HCID 136131615, Verbindung

Produkt 1

HCID 59427282HCID 59427282, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A microwave reaction vial was charged with 4-chloroquinoline-7-carbonitrile (97.1 mg, 0.515 mmol), 4-(4-ethyl-6-phenylpyridazin-3-ylamino)phenol (150 mg, 0.515 mmol), cesium carbonate (252 mg, 0.772 mmol) and 2.6 mL of DMSO. The vial was sealed, and the reaction mixture was irradiated in the microwave at 150° C. for 15 min. Upon cooling the mixture was poured into water and the resulting solids were filtered and washed with water. The crude solids were dissolved in 90/10/1 CH2Cl2/MeOH/NH4OH and purified by silica gel chromatography, 5-100% 90/10/1: CH2Cl2 over 25 min which provided 4-(4-(4-ethyl-6-phenylpyridazin-3-ylamino)phenoxy)quinoline-7-carboxamide as a tan solid. MS m/z=462 [M+H]+. Calc'd for C28H23N3O2: 461.52.

Aufarbeitung

  1. customA microwave reaction
  2. customThe vial was sealed
  3. customthe reaction mixture was irradiated in the microwave at 150° C. for 15 min
  4. temperatureUpon cooling the mixture
  5. filtrationthe resulting solids were filtered
  6. washwashed with water
  7. dissolutionThe crude solids were dissolved in 90/10/1 CH2Cl2/MeOH/NH4OH
  8. custompurified by silica gel chromatography, 5-100% 90/10/1

Quellen und Nachweise

ORD-Eintrag
ord-02006fbc5cdf49e994d968e731efc9e8
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08557816B2

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