4-Amino-2,3,5,6-tetrafluorobenzonitrile → HCID 178462406, Verbindung

HRID 480960

Reaktionsgleichung

Reaktionsgleichung von HRID 480960
[NH2:1][C:2]1[C:9]([F:10])=[C:8]([F:11])[C:5]([C:6]#[N:7])=[C:4]([F:12])[C:3]=1[F:13].C[Al](C)C.[F:18][C:19]1[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:20]=1[C@@:26]([OH:52])([CH2:46][N:47]1[CH:51]=[N:50][CH:49]=[N:48]1)[C@H:27]([S:29][C@@H:30]1[CH2:35][O:34][C@@H:33]([C:36]2[CH:45]=[CH:44][C:39]([C:40](OC)=[O:41])=[CH:38][CH:37]=2)[O:32][CH2:31]1)[CH3:28]>>[C:6]([C:5]1[C:4]([F:12])=[C:3]([F:13])[C:2]([NH:1][C:40](=[O:41])[C:39]2[CH:44]=[CH:45][C:36]([C@H:33]3[O:32][CH2:31][C@H:30]([S:29][C@H:27]([CH3:28])[C@:26]([C:20]4[CH:21]=[CH:22][C:23]([F:25])=[CH:24][C:19]=4[F:18])([OH:52])[CH2:46][N:47]4[CH:51]=[N:50][CH:49]=[N:48]4)[CH2:35][O:34]3)=[CH:37][CH:38]=2)=[C:9]([F:10])[C:8]=1[F:11])#[N:7]

Komponenten

4

Edukt 3

HCID 873224-Amino-2,3,5,6-tetrafluorobenzonitrileHCID 16682925TrimethylaluminumHCID 178497884HCID 178497884, Verbindung

Produkt 1

HCID 178462406HCID 178462406, VerbindungAusbeute 42,2 %

Versuchsvorschrift

In the same manner as that described in Example 3(4), a reaction was carried out using commercially available 4-amino-2,3,5,6-tetrafluorobenzonitrile (227 mg, 1.2 mmol), trimethylaluminium (1.1 ml, 1.07M n-hexane solution, 1.2 mmol) and methyl 4-[trans-5-[[(1R,2R)-2-(2,4-difluorophenyl)-2-hydroxy-1-methyl-3-(1H-1,2,4-triazol-1-yl)propyl]thio]-1,3-dioxan-2-yl]benzoate (150 mg, 0.30 mmol), obtained in Example 12(1), and the reaction mixture was treated using a similar procedure to that described in Example 3(4) to afford the title compound (84 mg, yield 42%) as a colorless oil which was recrystallized from ethyl acetate-hexane to give white powdery crystals.

Aufarbeitung

  1. customobtained in Example 12(1)
  2. additionthe reaction mixture was treated

Quellen und Nachweise

ORD-Eintrag
ord-1834b2ab16ed4636b84db079228e8f88
Quelldatensatz
uspto-grants-2003_11
Patentnummer
US06653330B2

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