Diisopropylethylamine → N-Cyclopropyl-N-[1-(3-phenyl-[1,2,4]oxadiazol-5-yl)-piperidin-4-yl]-4-pyridin-4-yl-benzamide
Reaction equation
F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.C(N(C(C)C)C(C)C)C.[N:32]1[CH:37]=[CH:36][C:35]([C:38]2[CH:46]=[CH:45][C:41]([C:42]([OH:44])=O)=[CH:40][CH:39]=2)=[CH:34][CH:33]=1.[CH:47]1([NH:50][CH:51]2[CH2:56][CH2:55][N:54]([C:57]3[O:61][N:60]=[C:59]([C:62]4[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=4)[N:58]=3)[CH2:53][CH2:52]2)[CH2:49][CH2:48]1>CN(C)C=O>[CH:47]1([N:50]([CH:51]2[CH2:52][CH2:53][N:54]([C:57]3[O:61][N:60]=[C:59]([C:62]4[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=4)[N:58]=3)[CH2:55][CH2:56]2)[C:42](=[O:44])[C:41]2[CH:40]=[CH:39][C:38]([C:35]3[CH:34]=[CH:33][N:32]=[CH:37][CH:36]=3)=[CH:46][CH:45]=2)[CH2:49][CH2:48]1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
2-(1H-Benzotriazol-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate (75 mg) and ethyldiisopropylamine (74 μL) are added to a solution of 4-pyridin-4-yl-benzoic acid (42 mg) in N,N-dimethylformamide (5 mL) at room temperature. The solution is stirred for 10 min prior to the addition of cyclopropyl-[1-(3-phenyl-[1,2,4]oxadiazol-5-yl)-piperidin-4-yl]-amine (60 mg). The resulting mixture is stirred at 60° C. for 5 h, cooled to room temperature and concentrated in vacuo. The crude product is purified by HPLC (H2O/MeOH/TFA). LC (method 6): tR=1.44 min; Mass spectrum (ESI+): m/z=466 [M+H]+.
Workup
- stirringThe resulting mixture is stirred at 60° C. for 5 h
- concentrationconcentrated in vacuo
- customThe crude product is purified by HPLC (H2O/MeOH/TFA)
Sources & evidence
- ORD record
- ord-34e44206e1d9499f901298242fa9e8ba
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08822471B2
Reaction notes
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