6-Ethylpyridin-2-amine → HCID 86689738, compound

HRID 1396376Notes

Reaction equation

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

Participants

Conditions

Temperature: 140 °C

Procedure

4,6-Dichloro-pyridazine-3-carboxylic acid ethyl ester (500 mg, 2.26 mmol) and 6-ethylpyridin-2-amine 415 mg, 3.39 mmol) were dissolved in acetonitrile (7 mL), then heated at 140° C. for 3 d. The reaction mixture was cooled and concentrated in vacuo. Purification by chromatography (silica, 5 to 50% ethyl acetate in hexanes) gave 6-chloro-4-(6-ethyl-pyridin-2-ylamino)-pyridazine-3-carboxylic acid ethyl ester (246 mg, 35%) as a light brown solid. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 10.68 (br. s., 1H) 9.30 (s, 1H) 7.61 (t, J=7.8 Hz, 1H) 6.91 (d, J=7.3 Hz, 1H) 6.77 (d, J=7.8 Hz, 1H) 4.57 (q, J=7.2 Hz, 2H) 2.86 (q, J=7.6 Hz, 2H) 1.52 (t, J=7.1 Hz, 3H) 1.38 (t, J=7.5 Hz, 3H); LCMS (EI/CI) m/z: 307 [M+H].

Workup

temperatureThe reaction mixture was cooled
concentrationconcentrated in vacuo
customPurification by chromatography (silica, 5 to 50% ethyl acetate in hexanes)

Sources & evidence

ORD record: ord-3e48a01bf9c942e3a1f06b567dd15964
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08901124B2

Reaction notes

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