Potassium Carbonate → HCID 59716722, compound

HRID 2224285Notes

Reaction equation

HRID 2224285 reaction equation
[Cl:1][C:2]1[C:3]2[N:4]([C:15](=[O:18])[NH:16][N:17]=2)[N:5]=[CH:6][C:7]=1[C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=1.Cl[CH2:20][C:21]1[CH:22]=[CH:23][C:24]([C:27]([F:30])([F:29])[F:28])=[N:25][CH:26]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Cl:1][C:2]1[C:3]2[N:4]([C:15](=[O:18])[N:16]([CH2:20][C:21]3[CH:26]=[N:25][C:24]([C:27]([F:30])([F:28])[F:29])=[CH:23][CH:22]=3)[N:17]=2)[N:5]=[CH:6][C:7]=1[C:8]1[CH:9]=[CH:10][C:11]([CH3:14])=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27738105-(Chloromethyl)-2-(trifluoromethyl)pyridineHCID 59716808HCID 59716808, compound

Product 1

HCID 59716722HCID 59716722, compoundYield 59.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
55 °C

Procedure

To a stirring suspension of 8-chloro-7-p-tolyl-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-one (2.2 g, 8.4 mmol) and 5-(chloromethyl)-2-(trifluoromethyl)pyridine (2.1 g, 11 mmol) in DMF (15 mL) at room temperature under argon was added K2CO3 (1.74 g, 12.6 mmol). The resulting mixture was heated at 55° C. for 2 h. HPLC/MS analysis indicated complete reaction. The reaction mixture was concentrated under vacuum with co-evaporation of toluene (10 mL×2) to obtain a dark yellow solid. The crude product was purified by silica gel column chromatography (ISCO) eluting with hexanes/EtOAc/CH2Cl2. Desired product (2.1 g) was obtained as a brown solid. Washing with MeOH (10 mL×2) and drying provided pure title compound, 8-chloro-7-p-tolyl-2-((6-(trifluoromethyl)pyridin-3-yl)methyl)-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-one, (1.76 g, 56%) as a light yellow solid. MS [M+H]+ 420; HPLC retention time=3.53 min; 1HNMR (400 MHz, CDCl3) δ 8.89 (s, 1H), 8.13 (s, 1H), 8.00 (d, 1H), 7.70 (d, 1H), 7.30-7.50 (m, 4H), 5.36 (s, 2H), 2.45 (s, 3H).

Workup

  1. customreaction
  2. concentrationThe reaction mixture was concentrated under vacuum with co-evaporation of toluene (10 mL×2)
  3. customto obtain a dark yellow solid
  4. customThe crude product was purified by silica gel column chromatography (ISCO)
  5. washeluting with hexanes/EtOAc/CH2Cl2

Sources & evidence

ORD record
ord-5a7b5fc7b75f47e3aad9c611107dc5b8
Source dataset
uspto-grants-2008_05
Patent number
US07378418B2

Reaction notes

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