Reaction equation
C(N(CC)CC)C.O=[C:9]([CH:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1)[CH2:10][C:11]#[N:12].Cl.[CH:20]([NH:23][NH2:24])([CH3:22])[CH3:21]>C(O)C>[CH3:21][CH:20]([N:23]1[C:11]([NH2:12])=[CH:10][C:9]([CH:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)=[N:24]1)[CH3:22]Participants
Procedure
0.43 ml of triethylamine is added to a solution of 640 mg of 3-oxo-3-(tetrahydro-2H-pyran-4-yl)propanenitrile and 347 mg of isopropylhydrazine hydrochloride in 8 ml of ethanol under an argon atmosphere. The mixture is refluxed with magnetic stirring for 1 h and then concentrated to dryness under reduced pressure. The residue is taken up in 100 ml of ethyl acetate and the organic phase is washed twice with 40 ml of a saturated sodium hydrogen carbonate solution. The combined aqueous phases are extracted twice with 50 ml of ethyl acetate. The combined organic phases are dried over magnesium sulfate, filtered and concentrated under reduced pressure, so as to obtain 536 mg of 1-(propan-2-yl)-3-(tetrahydro-2H-pyran-4-yl)-1H-pyrazol-5-amine.
Workup
- temperatureThe mixture is refluxed
- concentrationconcentrated to dryness under reduced pressure
- washthe organic phase is washed twice with 40 ml of a saturated sodium hydrogen carbonate solution
- extractionThe combined aqueous phases are extracted twice with 50 ml of ethyl acetate
- dry with materialThe combined organic phases are dried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-2acc95365d0946c38ed57b369dd743ab
- Source dataset
- uspto-grants-2015_08
- Patent number
- US09115140B2
Linked notes
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