N-Hydroxy-4-(hydroxymethyl)benzimidamide → (4-{5-[2-(Methoxymethyl)-2'-methylbiphenyl-4-yl]-1,2,4-oxadiazol-3-yl}phenyl)methanol

HRID 219996Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 219996
[CH3:1][O:2][CH2:3][C:4]1[CH:9]=[C:8]([C:10]([OH:12])=O)[CH:7]=[CH:6][C:5]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH3:19].O[N:21]=[C:22]([C:24]1[CH:29]=[CH:28][C:27]([CH2:30][OH:31])=[CH:26][CH:25]=1)[NH2:23]>>[CH3:1][O:2][CH2:3][C:4]1[CH:9]=[C:8]([C:10]2[O:12][N:23]=[C:22]([C:24]3[CH:29]=[CH:28][C:27]([CH2:30][OH:31])=[CH:26][CH:25]=3)[N:21]=2)[CH:7]=[CH:6][C:5]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH3:19]

Komponenten

3

Edukt 2

HCID 53437716N-Hydroxy-4-(hydroxymethyl)benzimidamideHCID 594958222-(Methoxymethyl)-2'-methylbiphenyl-4-carboxylic acid

Produkt 1

HCID 59495741(4-{5-[2-(Methoxymethyl)-2'-methylbiphenyl-4-yl]-1,2,4-oxadiazol-3-yl}phenyl)methanol

Versuchsvorschrift

The title compound was obtained following procedure described for example 54 step 1 but starting from Intermediate 28 (248.00 mg; 0.90 mmol) and Intermediate 74 (150.00 mg; 0.90 mmol). Recrystallization from Et2O/pentane gave the title compound as a white powder. 1H NMR (DMSO-d6, 300 MHz) δ 8.32 (d, J=1.5 Hz, 1H), 8.16 (dd, J=7.9, 1.8 Hz, 1H), 8.10-8.07 (m, 2H), 7.55 (d, J=8.3 Hz, 2H), 7.41 (d, J=7.9 Hz, 1H), 7.36-7.26 (m, 3H), 7.15-7.13 (m, 1H), 5.38 (t, J=5.7 Hz, 1H), 4.61 (d, J=5.7 Hz, 1H), 4.22 (d, J=12.7 Hz, 1H), 4.15 (d, J=12.7 Hz, 1H), 3.25 (s, 3H), 2.03 (s, 3H). LC/MS (Method B): 387.2 (M+H)+. HPLC (Method A) Rt 5.51 min (Purity: 97.0%).

Aufarbeitung

  1. customRecrystallization from Et2O/pentane

Quellen und Nachweise

ORD-Eintrag
ord-b9e828a63752429bb514278cead586d9
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08202865B2

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