Dimethylformamide → HCID 59515563, compound

HRID 1160233Notes

Reaction equation

HRID 1160233 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13](=O)[NH:12][N:11]3C(=O)[N:16](C)[N:17]=[C:10]3[C:9]=2[C:20]2[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=2)=[CH:4][CH:3]=1.[C:26]([O-:29])([O-])=O.[K+].[K+].Br[CH2:33][C:34]1[CH:41]=[CH:40][C:37]([C:38]#[N:39])=[CH:36][CH:35]=1.CN(C=[O:46])C>C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]3[N:16]([C:26](=[O:29])[NH:11][N:12]=3)[N:17]([CH2:33][C:34]3[CH:41]=[CH:40][C:37]([C:38]#[N:39])=[CH:36][CH:35]=3)[C:10](=[O:46])[C:9]=2[C:20]2[CH:21]=[CH:22][N:23]=[CH:24][CH:25]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 869964-(Bromomethyl)benzonitrileHCID 68688231HCID 68688231, compound

Product 1

HCID 59515563HCID 59515563, compoundYield 18%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To the solution of 7-(4-chlorophenyl)-2-methyl-8-(pyridin-4-yl)-[1,2,4]triazolo[4,3-b]pyridazine-3,6(2H,5H)-dione (12 mg, 0.034 mmol), prepared as described in Example in DMF (0.5 ml) was added K2CO3 (7 mg, 0.05 mmol) followed by 4-(bromomethyl)benzonitrile (8 mg, 0.041 mmol). After 15 min, the reaction mixture was diluted with ethyl acetate. The resultant solution was washed with water. The organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure. The crude product was purified by reverse phase HPLC to give the title compound, 4-((8-(4-chlorophenyl)-3,6-dioxo-7-(pyridin-4-yl)-2,3-dihydro-[1,2,4]triazolo[4,3-b]pyridazin-5(6H)-yl)methyl)benzonitrile, (3.5 mg, 18%) as a mono trifluoroacetate salt as a yellow foam. MS M+H=455. 1H (CD3OD) δ 8.66(2H), 7.71-7.65(6H), 7.34-7.31(4H), 5.93(2H).

Workup

  1. washThe resultant solution was washed with water
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-5482706da61440d18f17ac868d807487
Source dataset
uspto-grants-2010_10
Patent number
US07816357B2

Reaction notes

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