N-(3-{1-Perhydro-2H-pyran-2-yl-5-[1-(triphenylmethyl)(1,2,4-triazol-3-yl)](1H-indazol-3-yl)}phenyl)-3-phenylpropanamide → N-[3-(5-(1H-1,2,4-Triazol-3-Yl)(1H-Indazol-3-Yl))Phenyl]-3-Propanamide

HRID 2183320Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2183320
O1CCCCC1[N:7]1[C:15]2[C:10](=[CH:11][C:12]([C:16]3[N:20]=[CH:19][N:18](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[N:17]=3)=[CH:13][CH:14]=2)[C:9]([C:40]2[CH:41]=[C:42]([NH:46][C:47](=[O:56])[CH2:48][CH2:49]C3C=CC=CC=3)[CH:43]=[CH:44][CH:45]=2)=[N:8]1>Cl.O1CCOCC1>[NH:18]1[CH:19]=[N:20][C:16]([C:12]2[CH:11]=[C:10]3[C:15](=[CH:14][CH:13]=2)[NH:7][N:8]=[C:9]3[C:40]2[CH:41]=[C:42]([NH:46][C:47](=[O:56])[CH2:48][CH3:49])[CH:43]=[CH:44][CH:45]=2)=[N:17]1

Komponenten

4

Edukt 1

HCID 22480348N-(3-{1-Perhydro-2H-pyran-2-yl-5-[1-(triphenylmethyl)(1,2,4-triazol-3-yl)](1H-indazol-3-yl)}phenyl)-3-phenylpropanamide

Produkt 1

HCID 178460023N-[3-(5-(1H-1,2,4-Triazol-3-Yl)(1H-Indazol-3-Yl))Phenyl]-3-PropanamideAusbeute 48 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

N-(3-{1-Perhydro-2H-pyran-2-yl-5-[1-(triphenylmethyl)(1,2,4-triazol-3-yl)](1H-indazol-3-yl)}phenyl)-3-phenylpropanamide 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 (0.049 g, 48% yield over 2 steps): 1H NMR (CD3OD) δ 8.73 (s, 1H), 8.40 (br s, 2H), 8.16 (s, 1H), 8.10 (d, 1H), 7.77-7.67 (m, 3H), 7.50 (t, 1H), 7.28 (d, 4H), 7.18 (sextet, 1H); ES-MS (m/z) 409.

Aufarbeitung

  1. extractionAfter neutralization with aqueous NaHCO3, the crude product was extracted in ethyl acetate
  2. custompurified by preparative HPLC (0.049 g, 48% yield over 2 steps)

Quellen und Nachweise

ORD-Eintrag
ord-2a661108c660412cbac176ae7a7e0ee4
Quelldatensatz
uspto-grants-2005_05
Patentnummer
US06897231B2

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