1,2-Dichloroethane → 4-(5-{3-[3-Ethyl-3-(3-hydroxy-phenyl)-azepan-1-yl]-3-oxo-propyl}-imidazol-1-ylmethyl)-2-fluoro-benzonitrile
Reaction equation
[C:1]([C:3]1[CH:19]=[CH:18][C:6]([CH2:7][N:8]2[C:12]([CH2:13][CH2:14][C:15]([OH:17])=O)=[CH:11][N:10]=[CH:9]2)=[CH:5][C:4]=1[F:20])#[N:2].[CH2:21]([C:23]1([C:30]2[CH:31]=[C:32]([OH:36])[CH:33]=[CH:34][CH:35]=2)[CH2:29][CH2:28][CH2:27][CH2:26][NH:25][CH2:24]1)[CH3:22].C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.CN1CCOCC1>CN(C=O)C>[CH2:21]([C:23]1([C:30]2[CH:35]=[CH:34][CH:33]=[C:32]([OH:36])[CH:31]=2)[CH2:29][CH2:28][CH2:27][CH2:26][N:25]([C:15](=[O:17])[CH2:14][CH2:13][C:12]2[N:8]([CH2:7][C:6]3[CH:18]=[CH:19][C:3]([C:1]#[N:2])=[C:4]([F:20])[CH:5]=3)[CH:9]=[N:10][CH:11]=2)[CH2:24]1)[CH3:22]Participants
7
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Procedure
3-[3-(4-Cyano-3-fluoro-benzyl)-3H-imidazol-4-yl]-propionic acid, as described above in Step E, (0.56 g, 0.78 mmol) and 3-(3-ethyl-azepan-3-yl)-phenol, as described above in Step J, (0.182 g, 0.78 mmol), HOBT (0.126 g, 0.936 mmol), EDC (0.179 g, 0.936 mmol) and N-methylmorpholine (0.257 mL, 2.34 mmol) were dissolved in DMF (15 mL) and stirred at ambient temperature for 18 h. The DMF was removed in vacuo and the residue was partitioned between EtOAc and saturated aqueous NaHCO3 solution. The organic layer was washed with H2O, brine, dried (MgSO4), filtered, and concentrated to give the title compound.
Workup
- customThe DMF was removed in vacuo
- customthe residue was partitioned between EtOAc and saturated aqueous NaHCO3 solution
- washThe organic layer was washed with H2O, brine
- dry with materialdried (MgSO4)
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-0e5f9eacc7174d699880c1ba3186aea6
- Source dataset
- uspto-grants-2001_11
- Patent number
- US06316436B1
Reaction notes
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