Hydrazine hydrate (1:1) → N-{1-[3-(4-Bromophenyl)-5-oxo-4,5-dihydro-1,2,4-triazin-6-yl]ethyl}acetamide

HRID 1270299Notes

Reaction equation

HRID 1270299 reaction equation
O.[NH2:2]N.Br.[Br:5][C:6]1[CH:11]=[CH:10][C:9]([C:12](=[NH:14])[NH2:13])=[CH:8][CH:7]=1.[C:15]([NH:18][CH:19]([CH3:27])[C:20](=O)[C:21](OCC)=[O:22])(=[O:17])[CH3:16]>C(O)C>[Br:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[NH:13][C:21](=[O:22])[C:20]([CH:19]([NH:18][C:15](=[O:17])[CH3:16])[CH3:27])=[N:2][N:14]=2)=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 24654Hydrazine hydrate (1:1)HCID 22245807Ethyl 3-acetamido-2-oxobutanoateHCID 22329612HCID 22329612, compound

Product 1

HCID 135553056N-{1-[3-(4-Bromophenyl)-5-oxo-4,5-dihydro-1,2,4-triazin-6-yl]ethyl}acetamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

3.50 ml of hydrazine hydrate (3.60 g, 27.5 mmol) are added to 4-bromobenzenecarboximidamide hydrobromide from example 3A (11.8 g) in 150 ml of ethanol, and the mixture is stirred for 1 h. After this time, ethyl 3-(acetylamino)-2-oxobutanoate from example 4A (16.8 g) in 76 ml of ethanol is added dropwise and the reaction mixture is stirred for 3 h at a bath temperature of 80° C., subsequently overnight at 20° C. The mixture is concentrated and the residue is purified by flash chromatography (eluent: dichloromethane/methanol 95:5).

Workup

  1. stirringthe reaction mixture is stirred for 3 h at a bath temperature of 80° C., subsequently overnight at 20° C
  2. concentrationThe mixture is concentrated
  3. customthe residue is purified by flash chromatography (eluent: dichloromethane/methanol 95:5)

Sources & evidence

ORD record
ord-550ec835241b4742868a26e73c677edd
Source dataset
uspto-grants-2007_04
Patent number
US07202243B2

Reaction notes

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