1,8-Diazabicyclo(5.4.0)undec-7-ene → 3-(4-Cyclopropyl-5-pyridin-4-yl-4H-[1,2,4]triazol-3-yl)-2-methyl-acrylic acid ethyl ester

HRID 732099

Reaktionsgleichung

[CH:1]1([N:4]2[C:8]([C:9]3[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=3)=[N:7][N:6]=[C:5]2[CH2:15]O)[CH2:3][CH2:2]1.[CH2:17]([O:19][C:20](=[O:31])[CH:21](P(OCC)(OCC)=O)[CH3:22])[CH3:18].C1CCN2C(=NCCC2)CC1>C(#N)C.O=[Mn]=O>[CH2:17]([O:19][C:20](=[O:31])[C:21]([CH3:22])=[CH:15][C:5]1[N:4]([CH:1]2[CH2:2][CH2:3]2)[C:8]([C:9]2[CH:10]=[CH:11][N:12]=[CH:13][CH:14]=2)=[N:7][N:6]=1)[CH3:18]

Komponenten

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

(4-cyclopropyl-5-pyridin-4-yl-4H-[1,2,4]triazol-3-yl)-methanol (6.8 g, 31.4 mmol) was mixed with MnO2 (40 g, 0.46 mol) in acetonitrile at r.t. for 2 hours and then heated at 80° C. for another 30 min. The reaction mixture was filtered through celite. The filtrate was mixed with 2-(diethoxy-phosphoryl)-propionic acid ethyl ester (12.35 g, 51.8 mmol) and DBU (7.17 g, 47 mmol) at 80 to 90° C. for 4 h. The reaction mixture was concentrated, dissolved in EA and washed with water and brine. The organic layer was dried, concentrated and triturated with hex. to give the title compound in 5.76 g (61%) yield. 1H-NMR: 8.78(d, 2H), 7.78 (d, 2H), 7.67 (s, 1H), 4.32 (q, 2H), 3.43 (m, 1H), 2.53 (s, 3H), 1.38 (t, 3H), 1.24 (m, 2H) and 0.73 (m, 2H).

Aufarbeitung

filtrationThe reaction mixture was filtered through celite
concentrationThe reaction mixture was concentrated
dissolutiondissolved in EA
washwashed with water and brine
customThe organic layer was dried
concentrationconcentrated
customtriturated with hex

Quellen und Nachweise

ORD-Eintrag: ord-17e9a081f4dc407bb38662c6b8452b97
Quelldatensatz: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07585881B2

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