Diethyl Malonate → Ethyl 2-(6-(3-chlorophenylamino)-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)acetate

HRID 446906Notes

Reaction equation

HRID 446906 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[N:10]=[N:11][C:12]([NH:15][NH2:16])=[CH:13][CH:14]=2)[CH:5]=[CH:6][CH:7]=1.[C:17](OCC)(=O)[CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20]>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[CH:14]=[CH:13][C:12]3[N:11]([C:17]([CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])=[N:16][N:15]=3)[N:10]=2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 7761Diethyl MalonateHCID 59363292N-(3-chlorophenyl)-6-hydrazinylpyridazin-3-amine

Product 1

HCID 59363294Ethyl 2-(6-(3-chlorophenylamino)-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)acetate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(Step 5-i) N-(3-chlorophenyl)-6-hydrazinylpyridazin-3-amine (1 g, 4.25 mmol)) was taken up in ethanol (10 mL) and diethyl malonate (2 g, 12.76 mmol) was added. After microirradiation at 150° C. for 30 min, the reaction mixture was concentrated to dryness, taken up in ethyl acetate, and filtered to give the product, ethyl 2-(6-(3-chlorophenylamino)-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)acetate, as a solid (1.1 g, 3.3 mmol, 78% yield).

Workup

  1. concentrationthe reaction mixture was concentrated to dryness
  2. filtrationfiltered

Sources & evidence

ORD record
ord-16a5358afd2543d7a545a84bf7dc7bc6
Source dataset
uspto-grants-2013_07
Patent number
US08481538B2

Reaction notes

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