(2R,3R)-3-(2,4-Difluorophenyl)-3-hydroxy-2-methyl-4-(1H-1,2,4-triazol-1-yl)thiobutyramide → HCID 10206981, Verbindung

HRID 429769Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 429769
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C@@:9]([OH:21])([CH2:15][N:16]1[CH:20]=[N:19][CH:18]=[N:17]1)[C@@H:10]([CH3:14])[C:11]([NH2:13])=[S:12].Br[CH2:23][C:24]([C:26]1[CH:31]=[CH:30][C:29]([C:32]2[N:33]=[N:34][S:35][CH:36]=2)=[CH:28][CH:27]=1)=O>C(#N)C.C(OCC)(=O)C>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C@:9]([OH:21])([C@H:10]([C:11]1[S:12][CH:23]=[C:24]([C:26]2[CH:27]=[CH:28][C:29]([C:32]3[N:33]=[N:34][S:35][CH:36]=3)=[CH:30][CH:31]=2)[N:13]=1)[CH3:14])[CH2:15][N:16]1[CH:20]=[N:19][CH:18]=[N:17]1

Komponenten

5

Edukt 2

HCID 10686541(2R,3R)-3-(2,4-Difluorophenyl)-3-hydroxy-2-methyl-4-(1H-1,2,4-triazol-1-yl)thiobutyramideHCID 183534182-Bromo-1-[4-(1,2,3-thiadiazol-4-yl)phenyl]ethanone

Produkt 1

HCID 10206981HCID 10206981, VerbindungAusbeute 45 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6342AcetonitrileLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of (2R,3R)-3-(2,4-difluorophenyl)-3-hydroxy-2-methyl-4-(1H-1,2,4-triazol-1-yl)thiobutyramide (19.7 mg) and 2-bromo-1-[4-(1,2,3-thiadiazol-4-yl)phenyl]ethanone (27.4 mg) in acetonitrile (3.0 ml) was stirred at room temperature for 1.0 hour. The solution was diluted with ethyl acetate (10 ml), washed with saturated sodium hydrogen carbonate solution (5 ml) and brine (5 ml), dried over anhydrous sodium sulfate, then concentrated in vacuo. The mixture was purified by silica gel column chromatography developed by hexane-ethyl acetate (1:1) to give (2R,3R)-2-(2,4-difluorophenyl)-3-{4-[4-(1,2,3-thiadiazol-4-yl)phenyl]thiazol-2-yl}-1-(1H-1,2,4-triazol-1-yl)butan-2-ol as a pale yellow solid (14.1mg). EI-MS: m/z 497 (M+); 1H-NMR (CDCl3): δ 1.26(3H, d, J=6.9 Hz), 4.10(1H, q, J=6.9 Hz), 4.31(1H, d, J=14.3 Hz), 4.92(1H, d, J=14.3 Hz), 6.04(1H, s), 6.76˜6.87 (2H, m), 7.48˜7.58(1H, m), 7.58(1H, s), 7.68(1H, s), 7.92(1H, s), 8.06(2H, d, J=8.4Hz), 8.16(2H, d, J=8.4 Hz), 8.73(1H, s).

Aufarbeitung

  1. washwashed with saturated sodium hydrogen carbonate solution (5 ml) and brine (5 ml)
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe mixture was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-28521b6502a14206bb43ed5eb90842d2
Quelldatensatz
uspto-grants-2001_11
Patentnummer
US06319933B1

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