Triethylamine → 2-tert-Butyl-5-pyridin-2-yl-2H-pyrazol-3-ylamine
Reaction equation
O=[C:2]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][N:7]=1)[CH2:3][C:4]#[N:5].C(N(CC)CC)C.Cl.[C:20]([NH:24][NH2:25])([CH3:23])([CH3:22])[CH3:21]>CCO.CCOC(C)=O>[C:20]([N:24]1[C:4]([NH2:5])=[CH:3][C:2]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][N:7]=2)=[N:25]1)([CH3:23])([CH3:22])[CH3:21]Participants
Procedure
To a stirred solution of 3-oxo-3-pyridin-2-yl-propionitrile (0.40 g, 2.7 mmol; CAS 54123-21-6) at r.t. in EtOH (10 ml) under an argon atmosphere were added triethylamine (1.1 ml, 8.2 mmol) and t-butylhydrazine hydrochloride (1.02 g, 8.2 mmol). The mixture was heated to reflux and stirring was continued for 2 hrs. The orange solution was cooled to r.t. The solids were filtered off. The filtrate was concentrated to leave an orange viscous oil which was taken up in EtOAc and washed with water. The aqueous layer was extracted with EtOAc and with CH2Cl2/MeOH 9:1. The combined organics were dried over MgSO4, filtered and concentrated. After silica gel chromatography using CH2Cl2/MeOH as gradient, the product was obtained as off-white solid (0.366 g, 62%).
Workup
- temperatureThe mixture was heated
- temperatureto reflux
- filtrationThe solids were filtered off
- concentrationThe filtrate was concentrated
- customto leave an orange viscous oil which
- washwashed with water
- extractionThe aqueous layer was extracted with EtOAc and with CH2Cl2/MeOH 9:1
- dry with materialThe combined organics were dried over MgSO4
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-acda246a8d9440a295ec7f6d081b381e
- Source dataset
- uspto-grants-2013_06
- Patent number
- US08470820B2
Reaction notes
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