Boron trifluoride etherate → HCID 178513157, compound

Temperature

100 °C

To a screw cap pressure vessel was added the intermediate from Step A (3.22 g, 10.2 mmol), aminoguanidine hydrochloride (1.69 g, 15.3 mmol), methanol (25 mL) and boron trifluoride diethyl etherate (2.6 mL, 20.4 mmol). The reaction solution was heated at 100° C. for 70 minutes. 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 hydrazone isomers. 1H NMR (400 MHz, CD3CN): δ 7.54 (d, J=8.4 Hz, 1H); 7.24-7.17 (m, 1H); 7.10 (d, J=2.6 Hz, 1H); 2.68-2.51 (m, 4H). m/z 371 (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

ORD record

ord-7858ae0047254cf0abba4fbc57cea805

Source dataset

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09365574B2