Reaktionsgleichung
[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][CH:8]=2)[N:3]=1.[CH3:14][O:15][C:16]1[CH:17]=[C:18]([CH:26]=O)[CH:19]=[C:20]2[C:25]=1[O:24][CH2:23][CH2:22][CH2:21]2.FC(F)(F)C(O)=O.[C:35](C1C=CC(NC(C2C=C(OC)C(OC)=CC=2F)C2NC(=O)N(C3C=CC=CC=3C(O)=O)N=2)=CC=1)(=N)[NH2:36].C[Si](C#N)(C)C.C(S([O-])(=O)=O)(F)(F)F.C(S([O-])(=O)=O)(F)(F)F.C(S([O-])(=O)=O)(F)(F)F.[Yb+3]>ClCCl>[CH3:14][O:15][C:16]1[CH:17]=[C:18]([CH:26]([NH:13][C:10]2[CH:11]=[CH:12][C:7]([C:4]3[N:3]=[C:2]([CH3:1])[O:6][N:5]=3)=[CH:8][CH:9]=2)[C:35]#[N:36])[CH:19]=[C:20]2[C:25]=1[O:24][CH2:23][CH2:22][CH2:21]2Komponenten
7
Edukt 5
HCID 82115Trimethylsilyl cyanide
HCID 2733225Ytterbium triflate
HCID 128319838-Methoxychromane-6-carbaldehyde
HCID 181881764-(5-Methyl-1,2,4-oxadiazol-3-yl)aniline
HCID 1363370832-{3-[(4-carbamimidoylphenylamino)-(2-fluoro-4,5-dimethoxyphenyl)methyl]5-oxo-4,5-dihydro-[1,2,4]triazol-1-yl}benzoic Acid TrifluoroacetateProdukt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
After adding 700 mg of 4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylamine, 770 mg of 8-methoxychromane-6-carbaldehyde [CAS No. 81258-23-3], 1g of MS3A and 1.1 ml of trimethylsilyl cyanide to a solution of 250 mg of Yb(OTf)3 in 5 ml of dichloromethane under a nitrogen atmosphere, the mixture was stirred overnight at room temperature. The reaction mixture was filtered through celite, and the celite was washed with 100 ml of ethyl acetate. The organic layer was concentrated under reduced pressure to give a crude product of (8-methoxychroman-6-yl)-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylamino]acetonitrile.
Aufarbeitung
- filtrationThe reaction mixture was filtered through celite
- washthe celite was washed with 100 ml of ethyl acetate
- concentrationThe organic layer was concentrated under reduced pressure
Quellen und Nachweise
- ORD-Eintrag
- ord-010dfd1d80a64cc7bc8e13e0d15a4805
- Quelldatensatz
- uspto-grants-2011_04
- Patentnummer
- US07928228B2
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