1,3-Dichloroacetone → HCID 178455314, Verbindung

HRID 1873568Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1873568
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([NH2:11])=[S:10])=[CH:4][CH:3]=1.Cl[CH2:13][C:14]([CH2:16]Cl)=O.[NH2:18][C:19]1[C:24]([C:25]#[N:26])=[C:23]([CH:27]2[CH2:32][CH2:31][CH:30]([O:33][Si:34]([C:37]([CH3:40])([CH3:39])[CH3:38])([CH3:36])[CH3:35])[CH2:29][CH2:28]2)[C:22]([C:41]#[N:42])=[C:21]([SH:43])[N:20]=1.C(=O)(O)[O-].[Na+]>CN(C=O)C>[NH2:18][C:19]1[C:24]([C:25]#[N:26])=[C:23]([C@H:27]2[CH2:28][CH2:29][C@@H:30]([O:33][Si:34]([C:37]([CH3:39])([CH3:40])[CH3:38])([CH3:35])[CH3:36])[CH2:31][CH2:32]2)[C:22]([C:41]#[N:42])=[C:21]([S:43][CH2:16][C:14]2[N:11]=[C:9]([NH:8][C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)[S:10][CH:13]=2)[N:20]=1

Komponenten

6

Edukt 4

HCID 107931,3-DichloroacetoneHCID 516892Sodium BicarbonateHCID 6930614-FluorophenylthioureaHCID 1784550312-Amino-4-(4-{[tert-butyl(dimethyl)silyl]oxy}cyclohexyl)-6-mercaptopyridine-3,5-dicarbonitrile

Produkt 1

HCID 178455314HCID 178455314, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

43 mg (0.26 mmol) of 4-fluorophenylthiourea and 31 mg (0.24 mmol) of 1,3-dichloroacetone are dissolved in 2 ml DMF and stirred at +80° C. for 3 h. After cooling to RT 93 mg (0.23 mmol) of the compound from Example 12A (cis isomer) and 78 mg (0.93 mmol) of sodium bicarbonate are added, and the reaction mixture is stirred at RT for 20 h. The mixture is then directly purified by preparative HPLC (column: YMC GEL ODS-AQ S-5/15 μm; mobile phase gradient: acetonitrile/water 10:90→95:5).

Aufarbeitung

  1. additionare added
  2. stirringthe reaction mixture is stirred at RT for 20 h
  3. customThe mixture is then directly purified by preparative HPLC (column: YMC GEL ODS-AQ S-5/15 μm; mobile phase gradient: acetonitrile/water 10:90→95:5)

Quellen und Nachweise

ORD-Eintrag
ord-bf5776ccca9143d58fd8430e59cbccb4
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08304412B2

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