5-(Azetidin-1-ylmethyl)-1-methyl-3-nitro-1H-pyrazole → 5-(Azetidin-1-ylmethyl)-1-methyl-1H-pyrazol-3-amine

A 500-mL Parr reactor bottle was purged with nitrogen and charged with 10% palladium on carbon (50% wet, 180 mg dry weight) and a solution of 21 (1.00 g, 5.10 mmol) in ethanol (100 mL). The bottle was attached to a Parr hydrogenator, evacuated, charged with hydrogen gas to a pressure of 50 psi and shaken for 2 h. After this time, the hydrogen was evacuated, and nitrogen was charged into the bottle. Celite 521 (1.0 g) was added, and the mixture was filtered through a pad of Celite 521. The filter cake was washed with ethanol (2×25 mL), and the combined filtrates were concentrated to dryness under reduced pressure to afford a 94% yield of 22 (800 mg) as a yellow oil: 1H NMR (300 MHz, CDCl3) δ 5.47 (s, 1H), 3.64 (s, 3H), 3.57 (br s, 2H), 3.43 (s, 2H), 3.19 (t, 4H, 0.1=7.2 Hz), 2.06 (quintet, 2H, J=7.2 Hz); MS (ESI+) m/z 167.1 (M+H).

1. customA 500-mL Parr reactor bottle was purged with nitrogen
2. additioncharged with 10% palladium on carbon (50% wet, 180 mg dry weight)
3. customevacuated
4. additioncharged with hydrogen gas to a pressure of 50 psi
5. customAfter this time, the hydrogen was evacuated
6. additionnitrogen was charged into the bottle
7. additionCelite 521 (1.0 g) was added
8. filtrationthe mixture was filtered through a pad of Celite 521
9. washThe filter cake was washed with ethanol (2×25 mL)
10. concentrationthe combined filtrates were concentrated to dryness under reduced pressure

ORD record

ord-cebbf3a6e5754999842a919490a87876

Source dataset

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08598174B2