Triethylamine → HCID 59835777, Verbindung

HRID 1916693Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1916693
CS(Cl)(=O)=O.[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:14]=[CH:15][C:16]([C:19]#[C:20][C:21]3[CH:30]=[CH:29][C:24]([O:25][CH2:26][CH2:27]O)=[CH:23][CH:22]=3)=[N:17][CH:18]=2)=[CH:9][CH:8]=1.[CH2:31]([N:33](CC)[CH2:34][CH3:35])[CH3:32].N1CC=CC1>C(Cl)Cl.CN(C=O)C>[Cl:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]2[CH:14]=[CH:15][C:16]([C:19]#[C:20][C:21]3[CH:30]=[CH:29][C:24]([O:25][CH2:26][CH2:27][N:33]4[CH2:34][CH:35]=[CH:32][CH2:31]4)=[CH:23][CH:22]=3)=[N:17][CH:18]=2)=[CH:11][CH:12]=1

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 660593-PyrrolineHCID 67363953HCID 67363953, Verbindung

Produkt 1

HCID 59835777HCID 59835777, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

23 μL (0.29 mmol) methanesulphonic acid chloride are added dropwise to a solution, cooled to 0° C., of 85 mg (0.24 mmol) 2-{4-[5-(4-chloro-phenyl)-pyridin-2-ylethynyl]-phenoxy}-ethanol and 41 μL (0.29 mmol) triethylamine in 10 mL DCM and the reaction mixture is stirred for 1 h at this temperature. 46 μL (0.58 mmol) 2,5-dihydro-1H-pyrrole are added dropwise, the mixture is heated to RT and stirred overnight. 1 mL of DMF is added and the mixture is heated for 8 h to 70° C. The mixture is evaporated down i. vac., the residue is combined with water, extracted exhaustively with EtOAc and the organic phase is dried over Na2SO4. After the desiccant and solvent have been eliminated the residue is purified by chromatography on silica gel (EtOAc/MeOH/NH3 95:5:0.5).

Aufarbeitung

  1. stirringstirred overnight
  2. temperaturethe mixture is heated for 8 h to 70° C
  3. customThe mixture is evaporated down i
  4. extractionextracted exhaustively with EtOAc
  5. dry with materialthe organic phase is dried over Na2SO4
  6. customis purified by chromatography on silica gel (EtOAc/MeOH/NH3 95:5:0.5)

Quellen und Nachweise

ORD-Eintrag
ord-fd4fb011defd4d3faa9d24e46d532073
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08618132B2

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