1,2,3,6-Tetrahydropyridine → 1-(1,3-Benzoxazol-5-ylcarbonyl)-1,2,3,6-tetrahydropyridine

HRID 442644

Reaktionsgleichung

Reaktionsgleichung von HRID 442644
[NH2:1][C:2]1C=[CH:9][C:5](C(O)=O)=[CH:4][C:3]=1O.[O:12]1[C:16]2[CH:17]=[CH:18][C:19]([C:21]([OH:23])=O)=[CH:20][C:15]=2[N:14]=[CH:13]1.C(OC(OCC)OCC)(=O)C.O1C2C=C(C(N3CC=CCC3)=O)C=CC=2N=C1.N1CC=CCC1>>[O:12]1[C:16]2[CH:17]=[CH:18][C:19]([C:21]([N:1]3[CH2:2][CH:3]=[CH:4][CH2:5][CH2:9]3)=[O:23])=[CH:20][C:15]=2[N:14]=[CH:13]1

Komponenten

6

Edukt 5

HCID 127501,2,3,6-TetrahydropyridineHCID 84166Methanol, 1,1-diethoxy-, 1-acetateHCID 1375664-Amino-3-hydroxybenzoic acidHCID 115359401-(1,3-Benzoxazol-6-ylcarbonyl)-1,2,3,6-tetrahydropyridine2×HCID 190067671,3-Benzoxazole-5-carboxylic acid

Produkt 1

HCID 116515261-(1,3-Benzoxazol-5-ylcarbonyl)-1,2,3,6-tetrahydropyridine

Versuchsvorschrift

4-Amino-3-hydroxybenzoic acid is converted into 1,3-benzoxazol-5-carboxylic acid by treating with diethoxymethyl acetate as described for the preparation of Invention Compound IX. EMIS m/z=163 (parent), 146 (base), 118, 90, and 63. Coupling of the acid with 1,2,3,6-tetrahydropyridine is performed in the same manner as described for the preparation of isomeric Invention Compound IX. 1H NMR δ 2.1-2.4 (br, 4), 3.4-4.3 (br m, 4), 5.5-5.95 (br m, 2), 7.45 (dd, 1, J=8.17, 1.41 Hz), 7.70 (d, 1, J=0.96 Hz), 7.83 (d, 1, J=8.16 Hz), and 8.18 ppm (s, 1).

Quellen und Nachweise

ORD-Eintrag
ord-0a3479216f8c4baaa93ce061d956fa91
Quelldatensatz
uspto-grants-1999_04
Patentnummer
US05891876

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