1,2-Dichloroethane → HCID 136337174, Verbindung

Temperatur

110 °C

Titanium (IV) chloride (0.39 mL, 3.5 mmol) was carefully added to a solution of 1-[(3,5-difluoro-phenylimino)-ethoxycarbonylamino-methyl]-1H-pyrazole-4-carboxylic acid ethyl ester (0.321 g, 0.876 mmol) and DCE (2.7 mL), and the resulting solution was heated to 110° C. for 1.5 h. The reaction mixture was cooled to room temperature and water (50 mL), methanol (1 mL), and DCM (40 mL) were added. The biphasic mixture was stirred for 30 min, and the layers were separated. The aqueous layer was further extracted with DCM (2×30 mL). The combined organic layers were washed with brine (40 mL), dried (MgSO4), and concentrated. The residue was triturated from EtOH to yield the titled compound (0.172 g, 60% yield). MS (ESI/Cl): mass calcd. for C14H10F2N4O3, 320.1; m/z found, 321.1 [M+H]+. 1H NMR (400 MHz, DMSO-d6): 13.09 (s, 1H), 8.99 (d, J=0.5 Hz, 1H), 8.35 (s, 1H), 7.42-7.32 (m, 2H), 4.30 (q, J=7.1 Hz, 2H), 1.32 (t, J=7.1 Hz, 3H).

1. temperatureThe reaction mixture was cooled to room temperature
2. customthe layers were separated
3. extractionThe aqueous layer was further extracted with DCM (2×30 mL)
4. washThe combined organic layers were washed with brine (40 mL)
5. dry with materialdried (MgSO4)
6. concentrationconcentrated
7. customThe residue was triturated from EtOH

ORD-Eintrag

ord-0897ad8ba2104191adec3a0e547b0057

Quelldatensatz

uspto-grants-2015_01

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08937078B2