Triethylamine → N,5-dimethyl-N-pyridazin-4-yl-1-[2,2,2-trifluoro-1-(trifluoromethyl)ethyl]pyrazole-4-carboxamide
Reaction equation
[CH3:1][C:2]1[N:6]([CH:7]([C:12]([F:15])([F:14])[F:13])[C:8]([F:11])([F:10])[F:9])[N:5]=[CH:4][C:3]=1[C:16]([OH:18])=O.[CH3:19][NH:20][C:21]1[CH:26]=[CH:25][N:24]=[N:23][CH:22]=1.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.C(N(CC)CC)C>C1COCC1>[CH3:19][N:20]([C:21]1[CH:26]=[CH:25][N:24]=[N:23][CH:22]=1)[C:16]([C:3]1[CH:4]=[N:5][N:6]([CH:7]([C:8]([F:9])([F:11])[F:10])[C:12]([F:14])([F:13])[F:15])[C:2]=1[CH3:1])=[O:18]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 22.5 °C
Procedure
A mixture of 300 mg 5-methyl-1-[2,2,2-trifluoro-1-(trifluoromethyl)ethyl]pyrazole-4-carboxylic acid, 127 mg N-methylpyridazin-4-amine, 710 mg O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetra-methyluronium hexafluorophosphate [HATU] and 220 mg triethylamine in 30 ml THF was stirred at 20-25° C. for about 24 h, then evaporated. The residue was taken up in 21 ml CH2Cl2, washed with 3×14 ml water, dried over Na2SO4, then evaporated. Purification by flash chromatography (CH2Cl2/MeOH) gave 130 mg of the title compound (90% purity).
Workup
- customevaporated
- washwashed with 3×14 ml water
- dry with materialdried over Na2SO4
- customevaporated
- customPurification by flash chromatography (CH2Cl2/MeOH)
Sources & evidence
- ORD record
- ord-c45ec1dd154c40858478d90d4f29803a
- Source dataset
- uspto-grants-2016_09
- Patent number
- US09439427B2
Reaction notes
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