Triethylamine → PF 04457845

HRID 1666330

Reaktionsgleichung

Cl.[NH:2]1[CH2:7][CH2:6][C:5](=[CH:8][C:9]2[CH:10]=[C:11]([CH:23]=[CH:24][CH:25]=2)[O:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][N:14]=2)[CH2:4][CH2:3]1.[N:26]1[CH:31]=[CH:30][CH:29]=[C:28]([NH:32][C:33](=O)[O:34]CC)[N:27]=1.NC1N=NC=CC=1.C(N(CC)CC)C>C(#N)C>[N:26]1[CH:31]=[CH:30][CH:29]=[C:28]([NH:32][C:33]([N:2]2[CH2:7][CH2:6][C:5](=[CH:8][C:9]3[CH:25]=[CH:24][CH:23]=[C:11]([O:12][C:13]4[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:20])[F:21])=[CH:15][N:14]=4)[CH:10]=3)[CH2:4][CH2:3]2)=[O:34])[N:27]=1

Komponenten

Reaktionsbedingungen

Temperatur: 180 °C

Versuchsvorschrift

2-(3-Piperidin-4-ylidenemethyl-phenoxy)-5-trifluoromethyl-pyridine hydrochloride (500 mg, 1.35 mmol, from Example 1, Step 5), ethyl pyridazin-3-ylcarbamate (248 mg, 1.48 mmol, prepared according to the procedure described in Synthesis, 1997, 1189-1194 from 3-aminopyridazine) and triethylamine (0.376 mL, 2.7 mmol) were combined in acetonitrile (4.5 mL) and heated in a microwave at 180° C. for 40 minutes. The reaction mixture was cooled to rt and concentrated to form a residue. The residue was purified by silica gel chromatography (50-100% EtOAc in CH2Cl2) to provide the title compound (340 mg). MS (APCI 10 V) AP+ 456.2, 376.2, 335.2; 1H NMR (400 MHz, CD3OD) δ ppm 2.54 (dt, J=50.71, 5.84 Hz, 4H) 3.64 (dt, J=36.50, 5.84 Hz, 4H) 6.47 (s, 1H) 6.96-7.07 (m, 2H) 7.08-7.20 (m, 2H) 7.40 (td, J=7.72, 0.52 Hz, 1H) 7.59 (dd, J=9.13, 4.62 Hz, 1H) 8.08 (dd, J=8.67, 2.68 Hz, 1H) 8.13 (d, J=8.92 Hz, 1H) 8.43 (dt, J=1.79, 0.81 Hz, 1H) 8.79 (d, J=4.19 Hz, 1H).

Aufarbeitung

temperatureThe reaction mixture was cooled to rt
concentrationconcentrated
customto form a residue
customThe residue was purified by silica gel chromatography (50-100% EtOAc in CH2Cl2)

Quellen und Nachweise

ORD-Eintrag: ord-9b9daba0256841a5a4aefe0ccabff597
Quelldatensatz: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08044052B2

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