HCID 874532, Verbindung → HCID 69748795, Verbindung

HRID 1062376Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1062376
[Cl:1][C:2]1[CH:7]=[C:6]([SH:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10](=[O:18])[C@:11]([OH:17])([CH3:16])[C:12]([F:15])([F:14])[F:13].I[C:20]1[CH:25]=[CH:24][C:23]([S:26]([N:29]2[CH2:33][CH2:32][CH2:31][CH2:30]2)(=[O:28])=[O:27])=[CH:22][CH:21]=1.C[O-].[Na+]>CC(N(C)C)=O.[Cu]Cl>[Cl:1][C:2]1[CH:7]=[C:6]([S:8][C:20]2[CH:25]=[CH:24][C:23]([S:26]([N:29]3[CH2:30][CH2:31][CH2:32][CH2:33]3)(=[O:28])=[O:27])=[CH:22][CH:21]=2)[CH:5]=[CH:4][C:3]=1[NH:9][C:10](=[O:18])[C@:11]([OH:17])([CH3:16])[C:12]([F:15])([F:13])[F:14]

Komponenten

6

Edukt 3

HCID 874532HCID 874532, VerbindungHCID 10942334Sodium MethoxideHCID 54333950HCID 54333950, Verbindung

Produkt 1

HCID 69748795HCID 69748795, VerbindungAusbeute 44,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 62652Cuprous chlorideKatalysatorHCID 31374DimethylacetamideLösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

Copper (1) chloride (0.038 g) was added to a mixture of (R)-N-(2-chloro-4-mercaptophenyl)-2-hydroxy-2-methyl-3,3,3-trifluoropropanamide (Example 210) (0.21 g), N-(4-iodobenzenesulphonyl)pyrrolidine (0.258 g) and sodium methoxide (0.042 g) in DMA (5 ml). The mixture was heated at 150° C. with stirring for 4 hours then cooled and the DMA removed by evaporation. Ethyl acetate (20 ml) and water (20 ml) was added and the mixture was filtered. The aqueous layer was extracted with ethyl acetate (3×20 ml) and the organic layers were combined and dried. Volatile material was removed by evaporation and the residue was purified on a silica gel Mega Bond Elut column, eluting with methanol/DCM 0-10% to give the title compound (0.16 g) as a solid. NMR (CDCl3): 1.75 (s, 3H), 1.75-1.85 (m, 4H), 3.2-3.3 (m, 4H), 4.0 (s, 1H), 7.2-7.3 (m, 2H), 7.4-7.45 (m, 1H), 7.6 (s, 1), 7.7 (d, 2H), 8.45 (d, 1H), 9.15 (s, 1H); MS (ESP−): 507.

Aufarbeitung

  1. temperaturethen cooled
  2. customthe DMA removed by evaporation
  3. additionEthyl acetate (20 ml) and water (20 ml) was added
  4. filtrationthe mixture was filtered
  5. extractionThe aqueous layer was extracted with ethyl acetate (3×20 ml)
  6. customdried
  7. customVolatile material was removed by evaporation
  8. customthe residue was purified on a silica gel Mega Bond Elut column
  9. washeluting with methanol/DCM 0-10%

Quellen und Nachweise

ORD-Eintrag
ord-acd0253acaae4a3d8aaba5c09bd405f7
Quelldatensatz
uspto-grants-2005_11
Patentnummer
US06960688B2

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