p-Toluenesulfonic acid → 4-(1H-Imidazol-1-yl)-2-(6-piperidin-1-ylpyrimidin-4-yl)-1,2-dihydro-3H-pyrazol-3-one
Reaction equation
C(O[C:4](=[O:15])[C:5]([N:10]1[CH:14]=[CH:13][N:12]=[CH:11]1)=[CH:6][N:7](C)C)C.[NH:16]([C:18]1[CH:23]=[C:22]([N:24]2[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]2)[N:21]=[CH:20][N:19]=1)N.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(OCC)(=O)C>[N:10]1([C:5]2[C:4](=[O:15])[N:16]([C:18]3[CH:23]=[C:22]([N:24]4[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]4)[N:21]=[CH:20][N:19]=3)[NH:7][CH:6]=2)[CH:14]=[CH:13][N:12]=[CH:11]1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
5.5 g (26.3 mmol) of the compound from Example 42A and 6.1 g (31.5 mmol) of the compound from Example 8A are dissolved in 55 ml ethyl acetate and 1.2 g (10.5 mmol) p-toluenesulfonic acid are added. The mixture is heated to the reflux and is stirred at this temperature for 16 h. After cooling to RT, the precipitate is filtered off and washed with ethyl acetate. The solid is dissolved in 50 ml water and the solution is adjusted to pH 7 with 1 N hydrochloric acid. The precipitate is filtered off, washed with water and diisopropyl ether and finally dried over phosphorus pentoxide.
Workup
- temperatureThe mixture is heated to the
- temperaturereflux
- filtrationthe precipitate is filtered off
- washwashed with ethyl acetate
- dissolutionThe solid is dissolved in 50 ml water
- filtrationThe precipitate is filtered off
- washwashed with water and diisopropyl ether
- dry with materialfinally dried over phosphorus pentoxide
Sources & evidence
- ORD record
- ord-91fe875019474c7ca477ef0141dff174
- Source dataset
- uspto-grants-2015_03
- Patent number
- US08987261B2
Reaction notes
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