1,3-Dichloroacetone → 2-Amino-4-[4-(2-{[tert-butyl(dimethyl)silyl]oxy}propoxy)phenyl]-6-[({2-[(4-fluorophenyl)amino]-1,3-thiazol-4-yl}methyl)thio]pyridine-3,5-dicarbonitrile

HRID 2362824Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2362824
[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]([C:27]2[CH:32]=[CH:31][C:30]([O:33][CH2:34][CH:35]([O:37][Si:38]([C:41]([CH3:44])([CH3:43])[CH3:42])([CH3:40])[CH3:39])[CH3:36])=[CH:29][CH:28]=2)[C:22]([C:45]#[N:46])=[C:21]([SH:47])[N:20]=1>CN(C=O)C>[NH2:18][C:19]1[C:24]([C:25]#[N:26])=[C:23]([C:27]2[CH:28]=[CH:29][C:30]([O:33][CH2:34][CH:35]([O:37][Si:38]([C:41]([CH3:42])([CH3:43])[CH3:44])([CH3:39])[CH3:40])[CH3:36])=[CH:31][CH:32]=2)[C:22]([C:45]#[N:46])=[C:21]([S:47][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

5

Edukt 3

HCID 107931,3-DichloroacetoneHCID 6930614-FluorophenylthioureaHCID 178458231HCID 178458231, Verbindung

Produkt 1

HCID 574320812-Amino-4-[4-(2-{[tert-butyl(dimethyl)silyl]oxy}propoxy)phenyl]-6-[({2-[(4-fluorophenyl)amino]-1,3-thiazol-4-yl}methyl)thio]pyridine-3,5-dicarbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 78.6 mg (0.46 mmol) of 4-fluorophenylthiourea and 56.0 mg (0.44 mmol) of 1,3-dichloroacetone in 2 ml of dry DMF is stirred at +80° C. for 3 h. After cooling to RT, 370 mg (0.42 mmol) of the compound from Example 42A are added, and the mixture is then stirred at RT for 20 h. The reaction mixture is purified directly by two preparative HPLCs (column: YMC GEL ODS-AQ S-5/15 μm; mobile phase gradient: acetonitrile/water 10:90→95:5).

Aufarbeitung

  1. customThe reaction mixture is purified directly by two preparative HPLCs (column: YMC GEL ODS-AQ S-5/15 μm; mobile phase gradient: acetonitrile/water 10:90→95:5)

Quellen und Nachweise

ORD-Eintrag
ord-cf004913e2d2418bb13fe22cb137f615
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08691850B2

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