Methylamine → N-((3-Isopropyl-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)methylene)methanamine

HRID 1930019Notes

Reaction equation

HRID 1930019 reaction equation
[CH:1]([C:4]1[N:8]2[N:9]=[C:10]([CH:13]=O)[CH:11]=[CH:12][C:7]2=[N:6][N:5]=1)([CH3:3])[CH3:2].[CH3:15][NH2:16].[O-]S([O-])(=O)=O.[Mg+2]>C(Cl)Cl>[CH:1]([C:4]1[N:8]2[N:9]=[C:10]([CH:13]=[N:16][CH3:15])[CH:11]=[CH:12][C:7]2=[N:6][N:5]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6329MethylamineHCID 24083Sulfuric acid magnesium salt (1:1)HCID 579298993-Isopropyl-[1,2,4]triazolo[4,3-b]pyridazine-6-carbaldehyde

Product 1

HCID 57929895N-((3-Isopropyl-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)methylene)methanamineYield 67%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a flask was added 3-isopropyl-[1,2,4]triazolo[4,3-b]pyridazine-6-carbaldehyde (0.420 g, 2.21 mmol, Preparation #2), and methylamine (40 wt % in water, 1.33 mL, 2.65 mmol) followed by MgSO4 (0.399 g, 3.31 mmol) in DCM (2 mL) to give an orange suspension. The mixture was stirred at ambient temperature for about 17 h. The mixture was filtered and concentrated in vacuo to afford the title compound (0.300 g, 67%): 1H NMR (DMSO-d6) δ 8.43 (s, 1H), 8.31 (d, 1H), 7.74 (d, 1H), 3.59 (m, 4H), 2.5 (s, 3H), 1.45 (d, 6H).

Workup

  1. customto give an orange suspension
  2. filtrationThe mixture was filtered
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8acbd06272cd4f4b96cc9838560617f0
Source dataset
uspto-grants-2012_05
Patent number
US08188083B2

Reaction notes

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