Dimethylamine → 7-(4-chlorophenyl)-2-((6-(dimethylamino)pyridin-3-yl)methyl)-8-(pyridin-4-yl)-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-one

HRID 2224243Notes

Reaction equation

HRID 2224243 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[N:12][N:11]3[C:14](=[O:25])[N:15]([CH2:17][C:18]4[CH:19]=[N:20][C:21](Cl)=[CH:22][CH:23]=4)[N:16]=[C:10]3[C:9]=2[C:26]2[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=2)=[CH:4][CH:3]=1.[CH3:32][NH:33][CH3:34]>O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[N:12][N:11]3[C:14](=[O:25])[N:15]([CH2:17][C:18]4[CH:19]=[N:20][C:21]([N:33]([CH3:34])[CH3:32])=[CH:22][CH:23]=4)[N:16]=[C:10]3[C:9]=2[C:26]2[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 674DimethylamineHCID 119899567-(4-chlorophenyl)-2-((6-chloropyridin-3-yl)methyl)-8-(pyridin-4-yl)-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-one

Product 1

HCID 119888797-(4-chlorophenyl)-2-((6-(dimethylamino)pyridin-3-yl)methyl)-8-(pyridin-4-yl)-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-oneYield 57%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 7-(4-chlorophenyl)-2-((6-(chloro)pyridin-3-yl)methyl)-8-(pyridin-4-yl)-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-one (30 mg, 0.0667 mmol), prepared as described in Example 245, and N,N-dimethyl amine in water (1.0 mL) was heated to reflux. After 8 h, the solution was cooled to RT. The reaction mixture was concentrated under reduced pressure. The reside was purified by reverse phase HPLC to give the title compound, 7-(4-chlorophenyl)-2-((6-(dimethylamino)pyridin-3-yl)methyl)-8-(pyridin-4-yl)-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-one, (17.5 mg, 57%) as a yellow solid. HPLC: 1.41 min; M+H=458; 1H NMR (CDCl3) δ 8.63 (2H, d, J=5.0 hz), 8.23 (1H, d, J=5.0 Hz), 8.17 (1H, s), 7.58 (1H, d, J=10.0 Hz), 7.33 (2H, d, J=10.0 Hz), 7.23 (2H, d, J=5.0 Hz), 7.09 (2H, d, J=10.0 Hz), 6.47 (1H, d, J=10.0 Hz), 5.08 (2H, s), 3.07 (6H, s).

Workup

  1. customprepared
  2. temperaturewas heated to reflux
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. customThe reside was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-34ab5d6f501c45f0b36ab132e297bd05
Source dataset
uspto-grants-2008_05
Patent number
US07378418B2

Reaction notes

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