Water → HCID 22381819, compound
Reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:7]([C:9]1[C:13]([N+:14]([O-:16])=[O:15])=[C:12]([C:17]([NH2:19])=[O:18])[NH:11][N:10]=1)[CH3:8].Cl[CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=1.O>C(#N)C>[CH2:7]([C:9]1[C:13]([N+:14]([O-:16])=[O:15])=[C:12]([C:17]([NH2:19])=[O:18])[N:11]([CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=2)[N:10]=1)[CH3:8]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
Caesium carbonate (1.414 kg, 4.34 mol) was added to a suspension of the title compound of example (4d) (800 g, 4.34 mol) in acetonitrile (51) and the mixture warmed to 60° C. 2-Chloromethylpyridine (664.7 g, 5.23 mol) was added and the reaction heated at 70° C. for 7 hours, then water (9.5 l) added and the reaction mixture cooled to 10° C. Granulation of this mixture gave a precipitate which was filtered and dried to afford 3-ethyl-4-nitro-1-(pyridin-2-yl)methyl-pyrazole-5-carboxamide (367 g). Sodium chloride (1.58 kg) was added to the filtrate and the solution extracted with ethyl acetate (4×1.75 l). The combined organic extracts were distilled to remove approximately 10 l of solvent, toluene (5.6 l) added over 35 minutes to the hot (69-76° C.) solution and the mixture allowed to cool. The resulting suspension was granulated at <10° C. for 30 minutes, filtered, the solid washed with ethyl acetate:toluene (50:50) 600 ml) and dried (60° C.) to afford the title compound (624 g 52%) as a light brown solid. δ (DMSOd6): 1.08 (3H,t), 3.02 (2H,q), 5.53 (2H,s), 7.34 (2H,m), 7.65 (1H,s), 7.82 (1H,m), 7.93 (1H,s), 8.52 (1H,d). LRMS: m/z 276 (M+1)+.
Workup
- temperaturethe reaction heated at 70° C. for 7 hours
- temperaturethe reaction mixture cooled to 10° C
- customGranulation of this mixture gave a precipitate which
- filtrationwas filtered
- customdried
Sources & evidence
- ORD record
- ord-2e8e6d4f02794032ab2117d6597d4716
- Source dataset
- uspto-grants-2001_03
- Patent number
- US06207829B1
Reaction notes
Loading…