Thiophenol → 1,1,1-trifluoro-2-(4-((2R)-2-((phenylsulfanyl)methyl)-4-(2-thiophenylsulfonyl)-1-piperazinyl)phenyl)-2-propanol

HRID 1972566Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1972566
CS(O[CH2:6][C@H:7]1[CH2:12][N:11]([S:13]([C:16]2[S:17][CH:18]=[CH:19][CH:20]=2)(=[O:15])=[O:14])[CH2:10][CH2:9][N:8]1[C:21]1[CH:26]=[CH:25][C:24]([C:27]([OH:33])([CH3:32])[C:28]([F:31])([F:30])[F:29])=[CH:23][CH:22]=1)(=O)=O.C(=O)([O-])[O-].[K+].[K+].[C:40]1([SH:46])[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1>C(#N)C>[F:30][C:28]([F:31])([F:29])[C:27]([C:24]1[CH:23]=[CH:22][C:21]([N:8]2[CH2:9][CH2:10][N:11]([S:13]([C:16]3[S:17][CH:18]=[CH:19][CH:20]=3)(=[O:14])=[O:15])[CH2:12][C@@H:7]2[CH2:6][S:46][C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)=[CH:26][CH:25]=1)([OH:33])[CH3:32]

Komponenten

5

Edukt 3

HCID 7969ThiophenolHCID 11430Potassium CarbonateHCID 86670301((2R)-4-(2-thiophenylsulfonyl)-1-(4-(2,2,2-trifluoro-1-hydroxy-1-methylethyl)phenyl)-2-piperazinyl)methyl methanesulfonate2×

Produkt 1

HCID 569327221,1,1-trifluoro-2-(4-((2R)-2-((phenylsulfanyl)methyl)-4-(2-thiophenylsulfonyl)-1-piperazinyl)phenyl)-2-propanolAusbeute 78 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

To a 5-mL microwave vial was added ((2R)-4-(thiophen-2-ylsulfonyl)-1-(4-(1,1,1-trifluoro-2-hydroxypropan-2-yl)phenyl)piperazin-2-yl)methyl methanesulfonate (0.200 g, 0.378 mmol, Intermediate B), potassium carbonate (0.105 g, 0.757 mmol), thiophenol (0.076 mL, 0.76 mmol, Aldrich, St. Louis, Mo.), and acetonitrile (3.0 mL). The vial was sealed and heated in an Initiator microwave reactor (Biotage AB, Inc., Uppsala, Sweden) at 140° C. for 40 min. The reaction mixture was filtered and the filtrate was concentrated. The crude product was purified by column chromatography (40 g of silica, 10 to 40% acetone in hexanes) to afford 1,1,1-trifluoro-2-(4-((2R)-2-((phenylsulfanyl)methyl)-4-(2-thiophenylsulfonyl)-1-piperazinyl)phenyl)-2-propanol (0.160 g) as a mixture of two isomers:

Aufarbeitung

  1. customThe vial was sealed
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated
  4. customThe crude product was purified by column chromatography (40 g of silica, 10 to 40% acetone in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-08922177c3e343e5b8fee1435bb586f2
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08431563B2

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