1,2-Dichloroethane → Isobutyric acid N'-(5-fluoro-pyridin-2-yl)-hydrazide

To a solution of 5-fluoro-2-hydrazinyl-pyridine (for reference procedure see WO 2010/022076, which is incorporated herein by reference in its entirety; 2.08 g, 16.4 mmol), isobutyric acid (1.82 mL, 19.6 mmol), and HOBt hydrate (251 mg, 1.64 mmol) in DCM (50 mL), EDC (3.76 g, 19.6 mmol) was added, and the resulting orange solution was stirred at room temperature for 18 h. Sat. aq. NaHCO3 (50 mL) was added, and the mixture was stirred vigorously for 15 min. The organics were washed with sat. aq. NaHCO3 (50 mL), passed through a hydrophobic frit, and concentrated under vacuum to leave a pale brown solid. The solid was suspended in Et2O (50 mL) and filtered, washing with Et2O (25 mL), to leave a white solid (1.48 g, 46%). The ethereal washings were concentrated under vacuum and the residue suspended in Et2O (10 mL), filtered, washed with Et2O (2×2 mL), to leave a white solid (330 mg, 10%). The solids were combined (1.81 g, 56%). 1H NMR (400 MHz, CDCl3): 1.23 (6H, d), 2.50 (1H, sept), 6.65 (1H, dd), 6.80 (1H, d), 7.29 (1H, ddd), 7.77 (1H, br s), 8.01 (1H, d).

1. stirringthe mixture was stirred vigorously for 15 min
2. washThe organics were washed with sat. aq. NaHCO3 (50 mL)
3. concentrationconcentrated under vacuum
4. customto leave a pale brown solid
5. filtrationfiltered
6. washwashing with Et2O (25 mL)

ORDレコード

ord-a68833523a4343eea2694cf8bd425649

出典データセット

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08835431B2