Hydrazine hydrate (1:1) → n-{1-[3-(1-Naphthyl)-5-oxo-4,5-dihydro-1,2,4-triazin-6-yl]propyl}acetamide

HRID 1241492Notes

Reaction equation

HRID 1241492 reaction equation
Cl.[C:2]1([C:12](=[NH:14])[NH2:13])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][CH:3]=1.O.[NH2:16]N.[C:18]([NH:21][CH:22]([CH2:30][CH3:31])[C:23](=O)[C:24](OCC)=[O:25])(=[O:20])[CH3:19]>CS(C)=O.C(O)C>[C:2]1([C:12]2[NH:13][C:24](=[O:25])[C:23]([CH:22]([NH:21][C:18](=[O:20])[CH3:19])[CH2:30][CH3:31])=[N:16][N:14]=2)[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 24654Hydrazine hydrate (1:1)HCID 12301252Naphthalene-1-carboxamidine hydrochlorideHCID 21935058Ethyl 3-acetamido-2-oxopentanoate

Product 1

HCID 135594092n-{1-[3-(1-Naphthyl)-5-oxo-4,5-dihydro-1,2,4-triazin-6-yl]propyl}acetamide

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 702EthanolSolvent

Procedure

1.0 g (4.84 mmol, 1 equiv.) 1-Naphthalenecarboximidamide hydrochloride are suspended in 2 ml of DMSO and 0.29 g (5.81 mmol, 1.2 equiv.) hydrazine hydrate are added. After stirring at room temperature for 16 hours, 1.45 g (7.3 mmol, 1.5 equiv.) of the compound of Example 2A, dissolved in 10 ml of ethanol, are added. The reaction mixture is stirred at reflux for 1 hour and then at 60° C. (bath temperature) for 4 hours and then at room temperature over night. The mixture is evaporated to dryness in vacuo and the product is purified by flash chromatography.

Workup

  1. additionare added
  2. stirringThe reaction mixture is stirred
  3. temperatureat reflux for 1 hour
  4. waitat 60° C. (bath temperature) for 4 hours
  5. waitat room temperature over night
  6. customThe mixture is evaporated to dryness in vacuo
  7. customthe product is purified by flash chromatography

Sources & evidence

ORD record
ord-e1faec9c47e649ec9a24e6d9bf231d73
Source dataset
uspto-grants-2006_10
Patent number
US07115602B2

Reaction notes

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