Methyl 4,6-dichloropyridazine-3-carboxylate → HCID 86689754, compound

HRID 1396401Notes

Reaction equation

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

Participants

Conditions

Temperature: 80 °C

Procedure

A heavy walled resealable tube was charged with methyl 4,6-dichloropyridazine-3-carboxylate (1.3 g, 6.28 mmol) and 6-cyclobutylpyridin-2-amine (931 mg, 6.28 mmol) in acetonitrile (6.00 mL). The tube was heated with stirring in an oil bath at 80° C. for 48 h. Solvent was evaporated under vacuum, the residue was dissolved in dichloromethane and then purified by flash chromatography (spherical silica 20-45 μM, 50 g, Versaflash Supelco) eluting with 0 to 10% over 20 min dichloromethane/acetone to give methyl 6-chloro-4-(6-cyclobutylpyridin-2-ylamino)pyridazine-3-carboxylate (350 mg, 17.5% yield) as a light yellow solid. 1H NMR (CHLOROFORM-d) δ: 10.62 (s, 1H), 9.49 (s, 1H), 7.59 (t, J=7.9 Hz, 1H), 6.85 (d, J=7.6 Hz, 1H), 6.73 (d, J=8.3 Hz, 1H), 4.10 (s, 3H), 3.67 (quin, J=8.6 Hz, 1H), 2.24-2.58 (m, 4H), 1.85-2.22 (m, 2H); LC-MS 319.0 [M+H]+.

Workup

temperatureThe tube was heated
customSolvent was evaporated under vacuum
dissolutionthe residue was dissolved in dichloromethane
custompurified by flash chromatography (spherical silica 20-45 μM, 50 g, Versaflash Supelco)
washeluting with 0 to 10% over 20 min dichloromethane/acetone

Sources & evidence

ORD record: ord-e13a3f66fcea4a3cbf66190b64db34fa
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08901124B2

Reaction notes

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