2-Amino-6-methylpyridine → HCID 86689724, compound

HRID 1396356

Reaction equation

HRID 1396356 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].[CH3:14][C:15]1[N:20]=[C:19]([NH2:21])[CH:18]=[CH:17][CH:16]=1>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:21][C:19]1[CH:18]=[CH:17][CH:16]=[C:15]([CH3:14])[N:20]=1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 157652-Amino-6-methylpyridine2×HCID 53428795Ethyl 4,6-dichloropyridazine-3-carboxylate

Product 1

HCID 86689724HCID 86689724, compoundYield 36.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
140 °C

Procedure

4,6-Dichloro-pyridazine-3-carboxylic acid ethyl ester (300 mg, 1.36 mmol) and 6-methylpyridin-2-amine (176 mg, 1.63 mmol) were dissolved in acetonitrile (4.1 mL), then heated at 140° C. for 16 h. A second portion of 6-methylpyridin-2-amine (73 mg, 0.67 mmol) was added. After a further 2 d at 140° C. the reaction mixture was cooled and concentrated in vacuo. Purification by chromatography (silica, 5 to 40% ethyl acetate in hexanes) gave 6-chloro-4-(6-methyl-pyridin-2-ylamino)-pyridazine-3-carboxylic acid ethyl ester (146 mg, 36%) as a light yellow oil. 1H NMR (300 MHz, CHLOROFORM-d) δ ppm 10.68 (br. s., 1H) 9.21 (s, 1H) 7.59 (t, J=7.7 Hz, 1H) 6.90 (d, J=7.6 Hz, 1H) 6.76 (d, J=7.9 Hz, 1H) 4.57 (q, J=7.2 Hz, 2H) 2.57 (s, 3H) 1.51 (t, J=7.0 Hz, 3H); LCMS (EI/CI) m/z: 315 [M+Na].

Workup

  1. temperatureAfter a further 2 d at 140° C. the reaction mixture was cooled
  2. concentrationconcentrated in vacuo
  3. customPurification by chromatography (silica, 5 to 40% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-5d90b4441e0543f1b87875c82553e4f7
Source dataset
uspto-grants-2014_12
Patent number
US08901124B2

Linked notes

Loading…