Hydrazine hydrate (1:1) → 3-Amino-6-(1-propanoyl-4-piperidyl)pyrazine-2-carbohydrazide

Participants

Reaction Conditions

Reaction Steps

Methyl 3-amino-6-(1-propanoyl-4-piperidyl)pyrazine-2-carboxylate (110 mg, 0.38 mmol) was suspended in EtOH (2 mL) and hydrazine hydrate (94 mg, 92 μL, 1.9 mmol) was added and the reaction mixture was heated at 70° C. for 1.5 h, followed by 16 h heating at 35° C. forming a thick yellow solid. The solid was isolated by filtration, washed with water (20 mL) and ethanol (40 mL). The solid was dried under high vacuum to yield 3-amino-6-(1-propionylpiperidin-4-yl)pyrazine-2-carbohydrazide (105 mg, 95%) as a light yellow solid. 1H NMR (400 MHz, DMSO-d6) δ 9.70 (s, 1H), 8.12 (s, 1H), 7.27 (bs, 2H), 4.57-4.43 (m, 3H), 3.94 (d, J=13.6 Hz, 1H), 3.33 (bs, 2H), 3.13-2.97 (m, 1H), 2.90-2.76 (m, 1H), 2.58 (t, J=11.7 Hz, 1H), 2.34 (q, J=7.4 Hz, 2H), 1.83-1.70 (m, 3H), 1.69-1.55 (m, 1H), 1.01 (t, J=7.4 Hz, 3H). LC/MS m/z 293.3 [M+H]+.

Provenance & Evidence