HCID 9942188, compound → HCID 86689790, compound

HRID 1396451Notes

Reaction equation

HRID 1396451 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].[CH:14]([C:17]1[N:22]=[C:21]([NH2:23])[CH:20]=[C:19]([CH3:24])[CH:18]=1)([CH3:16])[CH3:15]>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:23][C:21]2[CH:20]=[C:19]([CH3:24])[CH:18]=[C:17]([CH:14]([CH3:16])[CH3:15])[N:22]=2)[CH:7]=1

Participants

4

Reactant 2

HCID 9942188HCID 9942188, compoundHCID 53428795Ethyl 4,6-dichloropyridazine-3-carboxylate

Product 1

HCID 86689790HCID 86689790, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
140 °C

Procedure

To a solution of ethyl 4,6-dichloropyridazine-3-carboxylate (260 mg, 1.18 mmol) in acetonitrile (3.9 mL) was added 6-isopropyl-4-methylpyridin-2-amine (265 mg, 1.76 mmol) and then the mixture heated at 140° C. for 48 h. The mixture was cooled, concentrated in vacuo, and then purified by chromatography (silica, 5 to 30% ethyl acetate in hexanes) to give ethyl 6-chloro-4-(6-isopropyl-4-methylpyridin-2-ylamino)pyridazine-3-carboxylate (117 mg, 349 μmol, 30%) as an off white solid. 1H NMR (400 MHz, CHLOROFORM-d6) δ ppm 10.60 (s, 1H), 9.39 (s, 1H), 6.76 (s, 1H), 6.59 (s, 1H), 4.58 (q, J=7.0 Hz, 2H), 3.04 (m, 1H), 2.35 (s, 3H), 1.53 (t, J=7.1 Hz, 3H), 1.35 (d, J=7.0 Hz, 6H), MS (EI/CI) m/z: 335.0 [M+H].

Workup

  1. temperatureThe mixture was cooled
  2. concentrationconcentrated in vacuo
  3. custompurified by chromatography (silica, 5 to 30% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-ce48e025b52a488ca51bfd9721281021
Source dataset
uspto-grants-2014_12
Patent number
US08901124B2

Reaction notes

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