Reaktionsgleichung
[F:1][C:2]1[CH:3]=[C:4]([C:8]2([N:15]([CH3:17])[CH3:16])[CH2:13][CH2:12][CH:11]([NH2:14])[CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.[Cl:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[C:25]1[C:29]([C:30](Cl)=[O:31])=[C:28]([CH3:33])[O:27][N:26]=1>>[CH3:16][N:15]([CH3:17])[C:8]1([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=2)[CH2:13][CH2:12][CH:11]([NH:14][C:30]([C:29]2[C:25]([C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=3[Cl:18])=[N:26][O:27][C:28]=2[CH3:33])=[O:31])[CH2:10][CH2:9]1Komponenten
3
Versuchsvorschrift
As described for Example 118, the polar diastereoisomer of 1-(3-fluorophenyl)-N,N-dimethylcyclohexane-1,4-diamine (350 mg) was reacted with 400 mg 3-(2-chlorophenyl)-5-methylisoxazole-4-carbonylchloride and worked up in a similar manner. The resultant crude product (590 mg) was chromatographed on silica gel (4.0×15 cm) with ethyl acetate/n-hexane/methanol (V:V=1:1:1). 440 mg of the polar diastereoisomer of 3-(2-chlorophenyl)-5-methylisoxazole-4-carboxylic acid [4-dimethylamino-4-(3-fluorophenyl)cyclohexyl]amide were obtained which, dissolved in 90 ml 2-butanone, were converted overnight into the corresponding hydrochloride by adding 17 μl water and 120 μl chlorotrimethylsilane (460 mg of white solid, Mp. 209-211° C.).
Aufarbeitung
- customThe resultant crude product (590 mg) was chromatographed on silica gel (4.0×15 cm) with ethyl acetate/n-hexane/methanol (V:V=1:1:1)
Quellen und Nachweise
- ORD-Eintrag
- ord-14ca6306c8f748828ff64579126b26eb
- Quelldatensatz
- uspto-grants-2012_01
- Patentnummer
- US08093272B2
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