HCID 16780526, compound → HCID 16780512, compound

Participants

Reaction Steps

5-Isobutyl-4-nitro-1H-pyrazol-3-carboxylic acid amide (4.7 g, 22 mmol) and 10% palladium on carbon (300 mg) in ethanol (80 ml) was stirred under hydrogen (60 psi) at room temperature for 4 hours, and held under nitrogen for 64 hours. The reaction mixture was filtered and the filtrate was concentrated under reduced pressure of dichloromethane:methanol (100:0 changing to 95:5 then 90:10, by volume) to give 4-amino-5-isobutyl-1H-pyrazol-3-carboxylic acid amide (3.8 g) as an off-white solid, which was a mixture of rotamers. 1H NMR (400 MHz, DMSO-D6): δ=12.20-12.28 (1H, brs), 7.00-7.10 (1.34H, brs), 6.80-6.85 (0.66H, brs), 4.27-4.40 (2H, brs), 2.27-2.36 (2H, d), 1.78-1.88 (1H, m), 0.77-0.84 (6H, d) ppm. LRMS (electrospray): m/z [M+H]+ 183, [M+Na]+ 205. Anal. Found C, 52.27; H, 7.78; N, 30.59. C8H14N4O requires C, 52.73; H, 7.76; N, 30.75%.

Provenance & Evidence