Boron trifluoride etherate → HCID 178513156, Verbindung

Temperatur

100 °C

To a screw cap pressure vessel was added the intermediate from Step B (0.450 g, 1.2 mmol), aminoguanidine hydrochloride (0.456 g, 6.2 mmol), methanol (20 mL) and boron trifluoride diethyl etherate (0.94 mL, 7.4 mmol). The reaction solution was heated at 100° C. for 3 hours. The solution was concentrated and the residue partitioned between EtOAc and aqueous 1N NaOH. The organic phase was washed twice with aqueous 1N NaOH and brine (1×). The organic phase was dried over anhydrous magnesium sulfate, filtered and concentrated to give the indicated compound as a mixture of E,Z hyrazone isomers. 1H NMR (500 MHz, CH3OH-d4): δ 7.60 (d, J=8.6 Hz, 1H); 7.26-7.23 (m, 1H); 7.18 (d, J=2.5 Hz, 1H); 2.74 (s, 2H); 2.56 (s, 2H). m/z=421.2 (M+H).

1. customTo a screw cap pressure vessel
2. concentrationThe solution was concentrated
3. customthe residue partitioned between EtOAc and aqueous 1N NaOH
4. washThe organic phase was washed twice with aqueous 1N NaOH and brine (1×)
5. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
6. filtrationfiltered
7. concentrationconcentrated
8. customto give the indicated compound
9. additionas a mixture of E,Z hyrazone isomers

ORD-Eintrag

ord-04af3ed8111f40aa97bd75802e5ce216

Quelldatensatz

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09365574B2