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 1353877

Reaktionsgleichung

Reaktionsgleichung von HRID 1353877
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-fef12e8f789c4c4ca5630f5ed3d972d9
Quelldatensatz
uspto-grants-2007_05
Patentnummer
US07220771B2

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