Ethyl 4,6-dichloropyridazine-3-carboxylate → HCID 86689812, compound

HRID 1396487Notes

Reaction equation

HRID 1396487 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]([C:17]1[CH:18]=[CH:19][C:20]([NH2:25])=[N:21][C:22]=1[O:23][CH3:24])([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:25][C:20]2[CH:19]=[CH:18][C:17]([CH:14]([CH3:16])[CH3:15])=[C:22]([O:23][CH3:24])[N:21]=2)[CH:7]=1

Participants

4

Reactant 2

HCID 53428795Ethyl 4,6-dichloropyridazine-3-carboxylateHCID 86689811HCID 86689811, compound

Product 1

HCID 86689812HCID 86689812, compoundYield 28.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of ethyl 4,6-dichloropyridazine-3-carboxylate (1.47 g, 6.64 mmol) in acetonitrile (7.6 mL) was added 5-isopropyl-6-methoxypyridin-2-amine (830 mg, 4.99 mmol) and the mixture heated at 100° C. in a sealed tube for 18 h. Upon completion, the mixture was concentrated onto silica gel and purified by chromatography (silica, 10% to 80% ethyl acetate in hexanes) to give ethyl 6-chloro-4-(5-isopropyl-6-methoxypyridin-2-ylamino)pyridazine-3-carboxylate (500 mg, 28.5%). MS (EI/CI) m/z: 351.2 [M+H].

Workup

  1. concentrationUpon completion, the mixture was concentrated onto silica gel
  2. custompurified by chromatography (silica, 10% to 80% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-b78acf029a3d49909cfaba344be32628
Source dataset
uspto-grants-2014_12
Patent number
US08901124B2

Reaction notes

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