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

HRID 1959478Notes

Reaction equation

[NH2:1][C:2]1[C:3]([C:18]([O:20]C)=O)=[N:4][C:5]([CH:8]2[CH2:13][CH2:12][N:11]([C:14](=[O:17])[CH2:15][CH3:16])[CH2:10][CH2:9]2)=[CH:6][N:7]=1.O.[NH2:23][NH2:24]>CCO>[NH2:1][C:2]1[C:3]([C:18]([NH:23][NH2:24])=[O:20])=[N:4][C:5]([CH:8]2[CH2:9][CH2:10][N:11]([C:14](=[O:17])[CH2:15][CH3:16])[CH2:12][CH2:13]2)=[CH:6][N:7]=1

Participants

Conditions

Temperature: 70 °C

Procedure

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]+.

Workup

temperatureheating at 35° C.
customforming a thick yellow solid
customThe solid was isolated by filtration
washwashed with water (20 mL) and ethanol (40 mL)
customThe solid was dried under high vacuum

Sources & evidence

ORD record: ord-f0b5dc7eed034a20a9c287a1cf2bd869
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08410112B2

Reaction notes

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