Triethylamine → HCID 24965141, Verbindung

HRID 1666427

Reaktionsgleichung

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

Komponenten

Reaktionsbedingungen

Temperatur: 180 °C

Versuchsvorschrift

4-(3-(4-(Trifluoromethyl)phenoxy)benzylidene)piperidine hydrochloride (200 mg, 0.541 mmol, from Example 53, Step 5), ethyl pyridazin-3-ylcarbamate (99 mg, 0.595 mmol) and triethylamine (0.15 mL, 1.08 mmol) were combined in acetonitrile (4.5 mL) and heated in a microwave at 180° C. for 40 min. The reaction mixture was cooled to RT and concentrated. The residue was purified by silica gel chromatography (50-100% EtOAc in CH2Cl2) to provide the title compound (156 mg). MS APCI M+ 455.2, 375.2, 334.2 M− 454.1; 1H NMR (400 MHz, CD3OD) δ ppm 2.46 (td, J=5.81, 0.84 Hz, 2H) 2.56 (td, J=5.81, 0.84 Hz, 2H) 3.55-3.61 (m, 2H) 3.65-3.70 (m, 2H) 6.44 (s, 1H) 6.91-6.99 (m, 2H) 7.06-7.14 (m, J=8.32 Hz, 3H) 7.35-7.43 (m, 1H) 7.59 (dd, J=9.13, 4.68 Hz, 1H) 7.61-7.66 (m, J=9.08 Hz, 2H) 8.12 (d, J=9.30 Hz, 1H) 8.78 (d, J=4.68 Hz, 1H).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag: ord-1e54155de5d14f7aad42f4cdef4de57a
Quelldatensatz: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08044052B2

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