6-Ethoxy-2-pyridinamine → Ethyl 6-chloro-4-(6-ethoxypyridin-2-ylamino)pyridazine-3-carboxylate

HRID 1396429Notes

Reaction equation

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

Participants

Conditions

Temperature: 130 °C

Procedure

In a sealed reaction tube, 6-ethoxypyridin-2-amine (775 mg, 5.61 mmol) and ethyl 4,6-dichloropyridazine-3-carboxylate (620 mg, 2.8 mmol) were combined with acetonitrile (14 mL) and stirred at 130° C. for 36 h. The mixture was cooled, concentrated to a brown solid, and then chromatographed (80 g Silicycle column, eluent 0 to 10% acetone in dichloromethane, 20 min, then held at 10% for 10 min) to give ethyl 6-chloro-4-(6-ethoxypyridin-2-ylamino)pyridazine-3-carboxylate (40.3 mg, 125 μmol, 4%) as a white solid. MS (EI/CI) m/z: 323.2 [M+H].

Workup

temperatureThe mixture was cooled
concentrationconcentrated to a brown solid
customchromatographed (80 g Silicycle column, eluent 0 to 10% acetone in dichloromethane, 20 min
waitheld at 10% for 10 min

Sources & evidence

ORD record: ord-01f00baf8f974ba084760ea67e551324
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08901124B2

Reaction notes

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