Ethyl 4,6-dichloropyridazine-3-carboxylate → HCID 86689815, compound

HRID 1396491Notes

Reaction equation

HRID 1396491 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[N:4][C:3]=1[C:9]([O:11][CH2:12][CH3:13])=[O:10].[CH:14]([O:17][C:18]1[N:23]=[C:22]([NH2:24])[CH:21]=[CH:20][CH:19]=1)([CH3:16])[CH3:15]>C(#N)C>[Cl:8][C:6]1[N:5]=[N:4][C:3]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[C:2]([NH:24][C:22]2[CH:21]=[CH:20][CH:19]=[C:18]([O:17][CH:14]([CH3:16])[CH3:15])[N:23]=2)[CH:7]=1

Participants

4

Reactant 2

HCID 53428795Ethyl 4,6-dichloropyridazine-3-carboxylateHCID 66520405HCID 66520405, compound

Product 1

HCID 86689815HCID 86689815, compoundYield 13.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
130 °C

Procedure

To a solution of ethyl 4,6-dichloropyridazine-3-carboxylate (1.63 g, 7.36 mmol) in acetonitrile (25 mL) was added 6-isopropoxypyridin-2-amine (1.12 g, 7.36 mmol) and the mixture heated at 130° C. in a sealed tube for 60 h. Upon completion, the mixture was concentrated on to silica gel and purified by chromatography (20% to 66% EtOAc in hexanes) to give ethyl 6-chloro-4-(6-isopropoxypyridin-2-ylamino)pyridazine-3-carboxylate (330 mg, 13%). MS (EI/CI) m/z: 337.1 [M+H].

Workup

  1. concentrationUpon completion, the mixture was concentrated on to silica gel
  2. custompurified by chromatography (20% to 66% EtOAc in hexanes)

Sources & evidence

ORD record
ord-2505a53254724b5183293b5f4b35cd53
Source dataset
uspto-grants-2014_12
Patent number
US08901124B2

Reaction notes

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