Pyridazin-1-ium-1-amine → 2-(4-ethoxy-phenyl)-pyrazolo[1,5-b]pyridazine-3-carboxylic Acid Methyl Ester

HRID 982639Notes

Reaction equation

HRID 982639 reaction equation
N12CCCC=C1CCCCN2.[CH3:12][O:13][C:14](=[O:26])[C:15]#[C:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH2:24][CH3:25])=[CH:19][CH:18]=1.[NH2:27][N+:28]1[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=1>C(#N)C>[CH3:12][O:13][C:14]([C:15]1[C:16]([C:17]2[CH:18]=[CH:19][C:20]([O:23][CH2:24][CH3:25])=[CH:21][CH:22]=2)=[N:27][N:28]2[C:33]=1[CH:32]=[CH:31][CH:30]=[N:29]2)=[O:26]

Participants

5

Reactant 3

HCID 6413253Pyridazin-1-ium-1-amineHCID 9834010Diazabicyclo[5.4.0]undec-7-eneHCID 22562335Methyl 3-(4-ethoxyphenyl)propiolate

Product 1

HCID 542755002-(4-ethoxy-phenyl)-pyrazolo[1,5-b]pyridazine-3-carboxylic Acid Methyl Ester

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Diazabicyclo[5.4.0]undec-7-ene (1.47 ml, 2 eq) was added dropwise to a solution of methyl 3-(4-ethoxy-phenyl)-prop-2-ynoic acid (1.0 g) and 1-amino pyridazinium iodide2 (2.19 g) in acetonitrile (10 ml) under nitrogen and stirred for 5 h. Concentration and aqueous workup gave the title compound (1.2 g) as a sticky brown solid.

Workup

  1. concentrationConcentration and aqueous workup

Sources & evidence

ORD record
ord-804530f3299549f48ecfd79c1ddce031
Source dataset
uspto-grants-2005_03
Patent number
US06861429B2

Reaction notes

Loading…