Ethyl 4,6-dichloropyridazine-3-carboxylate → HCID 86689779, compound

HRID 1396435Notes

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].[CH3:14][O:15][C:16]1[CH:17]=[CH:18][C:19]([NH2:25])=[N:20][C:21]=1[CH2:22][CH2:23][CH3:24]>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:19]2[CH:18]=[CH:17][C:16]([O:15][CH3:14])=[C:21]([CH2:22][CH2:23][CH3:24])[N:20]=2)[CH:7]=1

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of ethyl 4,6-dichloropyridazine-3-carboxylate (1.9 g, 8.6 mmol) in acetonitrile (28.7 mL) was added 5-methoxy-6-propylpyridin-2-amine (1.43 g, 8.6 mmol) and the mixture heated at 70° C. for 72 h. The mixture was concentrated in vacuo then purified by chromatography (silica, 10 to 60% ethyl acetate in hexanes) to give ethyl 6-chloro-4-(5-methoxy-6-propylpyridin-2-ylamino)pyridazine-3-carboxylate (1.22 g, 3.48 mmol, 41%) as a yellow solid. 1H NMR (400 MHz, CHLOROFORM-d6) δ ppm 10.58 (s, 1H), 8.84 (s, 1H), 7.25 (d, J=8.7 Hz, 1H), 6.88 (d, J=8.5 Hz, 1H), 4.58 (q, J=7.3 Hz, 2H), 3.88 (s, 3H), 2.87 (t, J=7.5 Hz, 2H), 1.84 (m, 2H), 1.52 (t, J=7.3 Hz, 3H), 1.05 (t, J=7.1 Hz, 3H); MS (EI/CI) m/z: 351.0 [M+H].

Workup

concentrationThe mixture was concentrated in vacuo
customthen purified by chromatography (silica, 10 to 60% ethyl acetate in hexanes)

Sources & evidence

ORD record: ord-d5526e6df0e14659b89b47e519a6fbd0
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08901124B2

Reaction notes

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