Reaktion #307092

Reaktionsgleichung

Intermediate 6

3-methyl-4-(4-methyl-3-thienyl)benzoic acid

Intermediate 2

methyl 4-[amino(hydroxyimino)methyl]-3-fluorobenzoate

→

title compound

methyl 3-fluoro-4-{5-[3-methyl-4-(4-methyl-3-thienyl)phenyl]-1,2,4-oxadiazol-3-yl}benzoate

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe title compound was prepared following procedure
2. 2
   FiltrationThe reaction mixture was filtered through a SPE NH2 column (2 g)
3. 3
   Waschenrinsed with ACN
4. 4
   Waschenrinsed with ACN
5. 5
   SonstigeAfter evaporation of the solvents
6. 6
   Filtrationfiltrated
7. 7
   Waschenwashed with cHex
8. 8
   Sonstigedried under vacuo

Vorschrift

The title compound was prepared following procedure described for example 4, step 1, but starting from Intermediate 6 (116.2 mg; 0.50 mmol) and Intermediate 2 (106.1 mg; 0.50 mmol). The reaction mixture was filtered through a SPE NH2 column (2 g) and rinsed with ACN. The filtrate was passed through a SPE SCX column (2 g) and rinsed with ACN. After evaporation of the solvents, the crude product was suspended in ACN, filtrated and washed with cHex dried under vacuo, affording the title compound. 1H NMR (DMSO-d6, 300 MHz) δ 8.35-8.30 (m, 1H), 8.17 (d, J=1.3 Hz, 1H), 8.08-8.01 (m, 2H), 7.95 (dd, J=11.0, 1.3 Hz, 1H), 7.46-7.42 (m, 2H), 7.35 (dd, J=3.2, 1.1 Hz, 1H), 3.93 (s, 3H), 2.24 (s, 3H), 2.01 (s, 3H). LC/MS (Method B): 409.1 (M+H)+. HPLC (Method A) Rt 6.06 min (Purity: 93.6%).

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