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

HRID 1959478ノート

反応式

HRID 1959478 の反応式
[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

参加物

4

反応物 2

HCID 24654Hydrazine hydrate (1:1)HCID 66745330Methyl 3-amino-6-(1-propanoyl-4-piperidyl)pyrazine-2-carboxylate

生成物 1

HCID 667444223-Amino-6-(1-propanoyl-4-piperidyl)pyrazine-2-carbohydrazide収率 95%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
70 °C

実験手順

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]+.

後処理

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

出典と根拠

ORDレコード
ord-f0b5dc7eed034a20a9c287a1cf2bd869
出典データセット
uspto-grants-2013_04
特許番号
US08410112B2

反応ノート

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