1,1'-Carbonyldiimidazole → Tyclopyrazoflor
Reaction equation
[F:1][C:2]([F:12])([F:11])[CH2:3][CH2:4][S:5][CH2:6][CH2:7][C:8]([OH:10])=O.C(N1C=CN=C1)([N:15]1[CH:19]=[CH:18]N=C1)=O.Cl.N1C=CN=C1.[Cl:31][C:32]1(NCC)[CH:36]=[CH:35][N:34]([C:37]2[CH:38]=[N:39][CH:40]=[CH:41][CH:42]=2)[NH:33]1>C(#N)C>[Cl:31][C:32]1[C:36]([N:15]([CH2:19][CH3:18])[C:8](=[O:10])[CH2:7][CH2:6][S:5][CH2:4][CH2:3][C:2]([F:1])([F:12])[F:11])=[CH:35][N:34]([C:37]2[CH:38]=[N:39][CH:40]=[CH:41][CH:42]=2)[N:33]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 20 °C
Procedure
A 20 mL vial was charged with 3-((3,3,3-trifluropropyl)thio)propanoic acid (0.999 g, 4.94 mmol) and acetonitrile (5 mL). Carbonyldiimidazole (0.947 g, 5.84 mmol) (off-gassing) and 1H-imidazole hydrochloride (0.563 g, 5.39 mmol) were added and the reaction was stirred at 20° C. for 4 hours. 3-Chloro-N-ethyl-1-(pyridine-3-yl)-1H-pyrazol-amine (1.00 g, 4.49 mmol) was added and the reaction was stirred at 75° C. for 42 hours, at which point HPLC analysis indicated that the conversion was 96%. The reaction was cooled to 20° C. and concentrated to dryness. The residue was purified by flash column chromatography using 80% ethyl acetate/hexanes as eluent. Pure fractions were combined and concentrated to afford a light yellow solid (1.58 g, 86%).
Workup
- stirringthe reaction was stirred at 75° C. for 42 hours, at which point HPLC analysis
- temperatureThe reaction was cooled to 20° C.
- concentrationconcentrated to dryness
- customThe residue was purified by flash column chromatography
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-e74b9209e8914f11b90f7af26d804861
- Source dataset
- uspto-grants-2016_09
- Patent number
- US09434712B2
Reaction notes
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