2-(Methoxymethyl)-2'-methylbiphenyl-4-carboxylic acid → Ethyl 4-(2-fluoro-4-{5-[2-(methoxymethyl)-2'-methylbiphenyl-4-yl]-1,2,4-oxadiazol-3-yl}phenoxy)butanoate

HRID 219989Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 219989
[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].[NH2:20][C:21](=[N:38]O)[C:22]1[CH:36]=[CH:35][C:25]([O:26][CH2:27][CH2:28][CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])=[C:24]([F:37])[CH:23]=1>>[F:37][C:24]1[CH:23]=[C:22]([C:21]2[N:38]=[C:10]([C:8]3[CH:7]=[CH:6][C:5]([C:13]4[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=4[CH3:19])=[C:4]([CH2:3][O:2][CH3:1])[CH:9]=3)[O:12][N:20]=2)[CH:36]=[CH:35][C:25]=1[O:26][CH2:27][CH2:28][CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31]

Komponenten

3

Edukt 2

HCID 594958222-(Methoxymethyl)-2'-methylbiphenyl-4-carboxylic acidHCID 72307473Ethyl 4-{4-[amino(hydroxyimino)methyl]-2-fluorophenoxy}butanoate

Produkt 1

HCID 67529495Ethyl 4-(2-fluoro-4-{5-[2-(methoxymethyl)-2'-methylbiphenyl-4-yl]-1,2,4-oxadiazol-3-yl}phenoxy)butanoate

Versuchsvorschrift

The title compound was prepared following procedure described for example 4, step 1, but starting from Intermediate 28 (192.22 mg; 0.75 mmol) and Intermediate 66 (234.54 mg; 0.83 mmol). The reaction mixture was filtered through a SPE NH2 column (2×2 g) and rinsed with ACN. The filtrate was passed through a SPE SCX column (2×2 g) and rinsed with ACN. After evaporation of the solvents, the crude product was purified by flash chromatography (c-hex/(DCM/EtOAc 1:1) gradient from 1:0 to 1:1), affording the title compound as a colorless oil. 1H NMR (CDCl3) δ 8.41 (d, J=1.4 Hz, 1H), 8.15 (dd, J=7.8, 1.9 Hz, 1H), 7.95-7.90 (m, 2H), 7.36-7.23 (m, 4H), 7.14-7.05 (m, 2H), 4.27-4.13 (m, 6H), 3.33 (s, 3H), 2.57 (t, J=7.2 Hz, 2H), 2.19 (quint., J=6.6 Hz, 2H), 2.08 (s, 3H), 1.27 (t, J=7.2 Hz, 3H). LC/MS (Method B): 505.3 (M+H)+. HPLC (Method A) Rt 6.24 min (Purity: 98.9%).

Aufarbeitung

  1. customThe title compound was prepared following procedure
  2. filtrationThe reaction mixture was filtered through a SPE NH2 column (2×2 g)
  3. washrinsed with ACN
  4. washrinsed with ACN
  5. customAfter evaporation of the solvents
  6. customthe crude product was purified by flash chromatography (c-hex/(DCM/EtOAc 1:1) gradient from 1:0 to 1:1)

Quellen und Nachweise

ORD-Eintrag
ord-46ebd244d5c7480b80568ed7d0940490
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08202865B2

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