Hydrazine hydrate (1:1) → Ethyl 4-{6-[1-(acetylamino)propyl]-5-oxo-4,5-dihydro-1,2,4-triazin-3-yl}benzoate

HRID 1791182Notes

Reaction equation

HRID 1791182 reaction equation
Cl.[NH2:2][C:3](=[NH:15])[C:4]1[CH:14]=[CH:13][C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][CH:5]=1.O.[NH2:17]N.[C:19]([NH:22][CH:23]([CH2:31][CH3:32])[C:24](=O)[C:25](OCC)=[O:26])(=[O:21])[CH3:20]>C(O)C>[C:19]([NH:22][CH:23]([C:24]1[C:25](=[O:26])[NH:15][C:3]([C:4]2[CH:14]=[CH:13][C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][CH:5]=2)=[N:2][N:17]=1)[CH2:31][CH3:32])(=[O:21])[CH3:20]

Participants

5

Reactant 3

HCID 24654Hydrazine hydrate (1:1)HCID 12710118Benzoic acid, 4-(aminoiminomethyl)-, ethyl ester, hydrochloride (1:1)HCID 21935058Ethyl 3-acetamido-2-oxopentanoate

Product 1

HCID 135682026Ethyl 4-{6-[1-(acetylamino)propyl]-5-oxo-4,5-dihydro-1,2,4-triazin-3-yl}benzoate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

1.98 g (8.66 mmol) ethyl 4-[amino(imino)methyl]benzoate hydrochloride 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 ml 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-1e2a99234f7f4c078ff0b3dc5a472c6e
Source dataset
uspto-grants-2006_07
Patent number
US07074790B2

Reaction notes

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