4-Methyl-6-propylpyridin-2-amine → Ethyl 6-chloro-4-(4-methyl-6-propylpyridin-2-ylamino)pyridazine-3-carboxylate

HRID 1396469Notes

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

Participants

Conditions

Temperature: 130 °C

Procedure

To a solution of ethyl 4,6-dichloropyridazine-3-carboxylate (335 mg, 1.52 mmol) in acetonitrile (5 mL) was added 4-methyl-6-propylpyridin-2-amine (342 mg, 2.27 mmol) and the mixture heated in a sealed tube at 130° C. for 72 h. The mixture was cooled, concentrated in vacuo, and then purified by chromatography (silica, 10 to 35% ethyl acetate in hexanes) to give ethyl 6-chloro-4-(4-methyl-6-propylpyridin-2-ylamino)pyridazine-3-carboxylate (147 mg, 439 mmol, 29%) as a light brown solid. 1H NMR (400 MHz, CHLOROFORM-d6) δ ppm 10.61 (s, 1H), 9.26 (s, 1H), 6.74 (s, 1H), 6.61 (s, 1H), 4.58 (q, J=7.1 Hz, 2H), 2.76 (t, J=7.5 Hz, 1H), 2.35 (s, 3H), 1.84 (m, 2H), 1.53 (t, J=6.9 Hz, 3H), 1.03 (t, J=7.3 Hz, 3H), MS (EI/CI) m/z: 335.0 [M+H].

Workup

temperatureThe mixture was cooled
concentrationconcentrated in vacuo
custompurified by chromatography (silica, 10 to 35% ethyl acetate in hexanes)

Sources & evidence

ORD record: ord-8f72d540587643038cb85f9a030d0124
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08901124B2

Reaction notes

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