Diisopropylethylamine → 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.[Cl:13][C:14]1(NCC)[CH:18]=[CH:17][N:16]([C:19]2[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=2)[NH:15]1.[CH:28]([N:31](C(C)C)CC)(C)[CH3:29]>>[Cl:13][C:14]1[C:18]([N:31]([CH2:28][CH3:29])[C:8](=[O:10])[CH2:7][CH2:6][S:5][CH2:4][CH2:3][C:2]([F:1])([F:12])[F:11])=[CH:17][N:16]([C:19]2[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=2)[N:15]=1Participants
Conditions
- Temperature
- 27.5 °C
Procedure
A solution of 3-((3,3,3-trifluoropropyl)thio)propanoic acid (2.18 g, 10.78 mmol) and 3-chloro-N-ethyl-1-(pyridin-3-yl)-1H-pyrazol-amine (2.00 g, 8.98 mmol) was cooled to 5° C. diisopropylethylamine (5.15 mL, 29.6 mmol) was added dropwise at 0-5° C. over 30 min, followed by the addition of 2,4,6-tripropyl-trioxatriphosphinane-2,4,-trioxide (4.00 g, 12.6 mmol) over 30 minutes at 0-5° C. The reaction was allowed to warm to 25-30° C. and stirred for 2 hours. Upon reaction completion, the reaction mixture was cooled to 0-5° C. and quenched with water (12 mL). The layers were separated and the aqueous layer was extracted with ethyl acetate (30 mL). The combined organic layers were concentrated to afford the desired product as an oil (3.4 g, 94%). Characterization matched sample prepared by previous method.
Workup
- additionwas added dropwise at 0-5° C. over 30 min
- customUpon reaction completion
- temperaturethe reaction mixture was cooled to 0-5° C.
- customquenched with water (12 mL)
- customThe layers were separated
- extractionthe aqueous layer was extracted with ethyl acetate (30 mL)
- concentrationThe combined organic layers were concentrated
Sources & evidence
- ORD record
- ord-c8b5c319537d4be88ae8fb37324b8d61
- Source dataset
- uspto-grants-2016_02
- Patent number
- US09255082B2
Reaction notes
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