Hydrazine hydrate (1:1) → N-[1-(5-Oxo-3-phenyl-4,5-dihydro-1,2,4-triazin-6-yl)propyl]cyclopentanecarboxamide

HRID 7547

Reaction equation

HRID 7547 reaction equation
Cl.[C:2]1([C:8](=[NH:10])[NH2:9])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.[NH2:12]N.[CH:14]1([C:19]([NH:21][CH:22]([CH2:30][CH3:31])[C:23](=O)[C:24](OCC)=[O:25])=[O:20])[CH2:18][CH2:17][CH2:16][CH2:15]1>C(O)C>[O:25]=[C:24]1[C:23]([CH:22]([NH:21][C:19]([CH:14]2[CH2:18][CH2:17][CH2:16][CH2:15]2)=[O:20])[CH2:30][CH3:31])=[N:12][N:9]=[C:8]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[NH:10]1

Participants

5

Reactant 3

HCID 24654Hydrazine hydrate (1:1)HCID 80289Benzamidine, hydrochlorideHCID 21991319Ethyl 3-[(cyclopentylcarbonyl)amino]-2-oxopentanoate

Product 1

HCID 135752529N-[1-(5-Oxo-3-phenyl-4,5-dihydro-1,2,4-triazin-6-yl)propyl]cyclopentanecarboxamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

3.5 g (22.3 mmol, 1 equiv.) benzenecarboximidamide hydrochloride are suspended in 10 ml of ethanol and 1.37 g (26.8 mmol, 1.2 equiv.) hydrazine hydrate are added. After stirring at room temperature for 1 hour, 6.28 g (24.6 mmol, 1.1 equiv) of ethyl 3-[(cyclopentylcarbonyl)amino]-2-oxopentanoate (Example 99A), dissolved in 40 ml of ethanol, are added. The reaction mixture is stirred at 70° C. (bath temperature) for 4 hours. The mixture is evaporated to dryness in vacuo and the product is purified by chromatography (flash or column chromatography or preparative HPLC).

Workup

  1. additionare added
  2. stirringThe reaction mixture is stirred at 70° C. (bath temperature) for 4 hours
  3. customThe mixture is evaporated to dryness in vacuo
  4. customthe product is purified by chromatography (flash or column chromatography or preparative HPLC)

Sources & evidence

ORD record
ord-ac4239c9e35d4f9abbabb31f98870e4d
Source dataset
uspto-grants-2006_08
Patent number
US07087605B2

Linked notes

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