2-Cyclohexyl-N-(3-{1-perhydro-2H-pyran-2-yl-5-[1-(triphenylmethyl)(1,2,4-triazol-3-yl)](1H-indazol-3-yl)}phenyl)acetamide → N-[3-(5-(1H-1,2,4-Triazol-3-YL)(1H-indazol-3-YL))phenyl]-2-cyclohexylacetamide

HRID 2183318Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2183318
[CH:1]1([CH2:7][C:8]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]3[C:25]4[C:20](=[CH:21][CH:22]=[C:23]([C:26]5[N:30]=[CH:29][N:28](C(C6C=CC=CC=6)(C6C=CC=CC=6)C6C=CC=CC=6)[N:27]=5)[CH:24]=4)[N:19](C4CCCCO4)[N:18]=3)[CH:12]=2)=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1>Cl.O1CCOCC1>[NH:28]1[CH:29]=[N:30][C:26]([C:23]2[CH:24]=[C:25]3[C:20](=[CH:21][CH:22]=2)[NH:19][N:18]=[C:17]3[C:13]2[CH:12]=[C:11]([NH:10][C:8](=[O:9])[CH2:7][CH:1]3[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]3)[CH:16]=[CH:15][CH:14]=2)=[N:27]1

Komponenten

4

Edukt 1

HCID 224801082-Cyclohexyl-N-(3-{1-perhydro-2H-pyran-2-yl-5-[1-(triphenylmethyl)(1,2,4-triazol-3-yl)](1H-indazol-3-yl)}phenyl)acetamide

Produkt 1

HCID 178520226N-[3-(5-(1H-1,2,4-Triazol-3-YL)(1H-indazol-3-YL))phenyl]-2-cyclohexylacetamideAusbeute 34 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

2-Cyclohexyl-N-(3-{1-perhydro-2H-pyran-2-yl-5-[1-(triphenylmethyl)(1,2,4-triazol-3-yl)](1H-indazol-3-yl)}phenyl)acetamide was dissolved in 4 mL of 4.0 N HCl in 1,4-dioxane and the reaction was stirred at room temperature overnight. After neutralization with aqueous NaHCO3, the crude product was extracted in ethyl acetate and purified by preparative HPLC (0.034 g, 34% yield over 2 steps): 1H NMR (CD3OD) δ 8.75 (s, 1H), 8.38 (br s, 2H), 8.20 (s, 1H), 8.10 (d, 1H), 7.76 (td, 2H), 7.70 (d, 1H), 7.51 (t, 1H), 2.30 (d, 2H), 1.90 (m, 1H), 1.78 (m, 4H), 1.3 (m, 4H), 1.07 (m, 2H); ES-MS (m/z) 401 [M+H]+.

Aufarbeitung

  1. extractionAfter neutralization with aqueous NaHCO3, the crude product was extracted in ethyl acetate
  2. custompurified by preparative HPLC (0.034 g, 34% yield over 2 steps)

Quellen und Nachweise

ORD-Eintrag
ord-c003cbed967d4fa7b32b6ffacc50a4a9
Quelldatensatz
uspto-grants-2005_05
Patentnummer
US06897231B2

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