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

HRID 1791188Notes

Reaction equation

HRID 1791188 reaction equation
Cl.[Br:2][C:3]1[CH:4]=[C:5]([C:9](=[NH:11])[NH2:10])[CH:6]=[CH:7][CH:8]=1.O.[NH2:13]N.[C:15]([NH:18][CH:19]([CH2:27][CH3:28])[C:20](=O)[C:21](OCC)=[O:22])(=[O:17])[CH3:16]>C(O)C>[Br:2][C:3]1[CH:4]=[C:5]([C:9]2[NH:10][C:21](=[O:22])[C:20]([CH:19]([NH:18][C:15](=[O:17])[CH3:16])[CH2:27][CH3:28])=[N:13][N:11]=2)[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 24654Hydrazine hydrate (1:1)HCID 122077183-Bromobenzene-1-carboximidamide hydrochlorideHCID 21935058Ethyl 3-acetamido-2-oxopentanoate

Product 1

HCID 135594081n-{1-[3-(3-Bromophenyl)-5-oxo-4,5-dihydro-1,2,4-triazin-6-yl]propyl}acetamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

2.02 g (8.6 mmol, 1 equiv.) 3-bromobenzenecarboximidamide hydrochloride (Example 31A) are suspended in 50 ml of ethanol, and 1.47 g (10.2 mmol, 1.2 equiv.) hydrazine hydrate are added. After stirring at room temperature for 1 hour, 2.59 g (13 mmol, 1.5 equiv.) of the compound of Example 2A, dissolved in 10 l of ethanol, are added. The reaction mixture is stirred at 80° 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 chromatography (flash or column chromatography or preparative HPLC).

Workup

  1. additionare added
  2. stirringThe reaction mixture is stirred at 80° C. (bath temperature) for 4 hours
  3. waitat room temperature over night
  4. customThe mixture is evaporated to dryness in vacuo
  5. customthe product is purified by chromatography (flash or column chromatography or preparative HPLC)

Sources & evidence

ORD record
ord-22e1a08ab57f4e1e9d83778a11c66ea6
Source dataset
uspto-grants-2006_07
Patent number
US07074790B2

Reaction notes

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