Potassium Carbonate → HCID 89767420, Verbindung

HRID 1752514Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1752514
Cl.[CH3:2][O:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][N:8]=[C:7]2[C:13]([NH:15][CH2:16][CH:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1)=[O:14].C(=O)([O-])[O-].[K+].[K+].Cl[CH2:30][C:31]1[S:32][CH:33]=[C:34]([C:36]([O:38][CH3:39])=[O:37])[N:35]=1>C(#N)C.CCOC(C)=O>[CH3:2][O:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][N:8]=[C:7]2[C:13]([NH:15][CH2:16][CH:17]1[CH2:22][CH2:21][N:20]([CH2:30][C:31]2[S:32][CH:33]=[C:34]([C:36]([O:38][CH3:39])=[O:37])[N:35]=2)[CH2:19][CH2:18]1)=[O:14]

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 25067319Methyl 2-(chloromethyl)thiazole-4-carboxylateHCID 89767058HCID 89767058, Verbindung

Produkt 1

HCID 89767420HCID 89767420, VerbindungAusbeute 32,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6342AcetonitrileLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Finally, a mixture of compound 7b (637 mg, 1.96 mmoles) and potassium carbonate (813 mg, 5.88 mmoles) in acetonitrile (5 mL) was heated to reflux for 1 hour, then a solution of methyl 2-(chloromethyl)-1,3-thiazole-4-carboxylate (500 mg, 2.6 mmoles) in acetonitrile (5 mL) was added dropwise. The mixture was refluxed overnight then was cooled, diluted with EtOAc and filtered. The resulting solid was washed with water, dried and purified via flash chromatography (silica, from CHCl3 to CHCl3:MeOH 9:1) providing 280 mg (32% yield) of methyl 2-{[4-({[(5-methoxy-1H-indazol-3-yl)carbonyl]amino}methyl)piperidin-1-yl]methyl}-1,3-thiazole-4-carboxylate 7.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto reflux for 1 hour
  3. temperatureThe mixture was refluxed overnight
  4. temperaturethen was cooled
  5. filtrationfiltered
  6. washThe resulting solid was washed with water
  7. customdried
  8. custompurified via flash chromatography (silica, from CHCl3 to CHCl3:MeOH 9:1)

Quellen und Nachweise

ORD-Eintrag
ord-61e4897006d3432cb602c3dbac010733
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09163013B2

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