Water → 1-(3-Chloro-4,5,6,7-tetrahydropyrazolo[1,5-a]pyridin-2-yl)-5-diethylamino-4-pyrazolecarbonitrile
Reaction equation
[H-].[Na+].[NH2:3][C:4]1[N:8]([C:9]2[C:17]([Cl:18])=[C:12]3[CH2:13][CH2:14][CH2:15][CH2:16][N:11]3[N:10]=2)[N:7]=[CH:6][C:5]=1[C:19]#[N:20].I[CH2:22][CH3:23].O.O1CC[CH2:27][CH2:26]1>>[Cl:18][C:17]1[C:9]([N:8]2[C:4]([N:3]([CH2:22][CH3:23])[CH2:26][CH3:27])=[C:5]([C:19]#[N:20])[CH:6]=[N:7]2)=[N:10][N:11]2[CH2:16][CH2:15][CH2:14][CH2:13][C:12]=12Participants
6
Reactant 5
Product 1
Conditions
- Temperature
- 0 °C
Procedure
10.45 g (0.35 mol) Sodium hydride (80%) was added to 100 ml tetrahydrofuran and cooled to 0° C. In a nitrogen atmosphere, a suspension of 43.6 g (0.17 mol) 5-amino-1-(3-chloro-4,5,6,7-tetrahydropyrazolo-[1,5-a]pyridin-2-yl)-4-pyrazolecarbonitrile in 500 ml tetrahydrofuran was added dropwise. The mixture was stirred for 1.5 hours. Then 31.4 ml (0.38 mol) iodoethane in 20 ml tetrahydrofuran was added dropwise at 15° C. After stirring for three hours at 15° C., the mixture was cooled. Water was then added dropwise and the mixture extracted with ethyl acetate. The organic phase was separated, dried and concentrated. The residue was recrystallised from ethyl acetate.
Workup
- additionwas added dropwise
- stirringAfter stirring for three hours at 15° C.
- temperaturethe mixture was cooled
- extractionthe mixture extracted with ethyl acetate
- customThe organic phase was separated
- customdried
- concentrationconcentrated
- customThe residue was recrystallised from ethyl acetate
Sources & evidence
- ORD record
- ord-b42c5ef763784406993a2262dc13638e
- Source dataset
- uspto-grants-1999_02
- Patent number
- US05869686
Reaction notes
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