Methyl 4,6-dichloropyridazine-3-carboxylate → 6-Chloro-4-(5,6-dimethoxy-pyridin-2-ylamino)-pyridazine-3-carboxylic acid methyl ester

HRID 1396388Notes

Reaction equation

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

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of 4,6-dichloro-pyridazine-3-carboxylic acid methyl ester (1.0 g, 4.83 mmol) and 5,6-dimethoxypyridin-2-amine (968 mg, 6.28 mmol) was dissolved in acetonitrile (5 mL) and heated at 70° C. for 16 h. The mixture was concentrated in vacuo and the crude mass obtained was purified by chromatography (silica, 100-200 mesh, 10-70% ethyl acetate in hexane) to give 6-chloro-4-(5,6-dimethoxy-pyridin-2-ylamino)-pyridazine-3-carboxylic acid methyl ester (830 mg, 53%) as a yellow solid. LC-MS: 325.2 [M+H]+.

Workup

concentrationThe mixture was concentrated in vacuo
customthe crude mass obtained
customwas purified by chromatography (silica, 100-200 mesh, 10-70% ethyl acetate in hexane)

Sources & evidence

ORD record: ord-f1e839351b8d4c2484a06a2a82d9ec04
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08901124B2

Reaction notes

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