Reaction equation
[C:1]([C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[CH:6][CH:5]=1)([OH:3])=O.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.[CH3:26][NH:27][CH2:28][CH2:29][N:30]1[CH2:35][CH2:34][CH:33]([O:36][C:37](=[O:51])[NH:38][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][C:40]=2[C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)[CH2:32][CH2:31]1>C(Cl)Cl>[CH:8]([C:7]1[CH:10]=[CH:11][C:4]([C:1]([CH2:26][NH:27][CH2:28][CH2:29][N:30]2[CH2:35][CH2:34][CH:33]([O:36][C:37](=[O:51])[NH:38][C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][C:40]=3[C:45]3[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=3)[CH2:32][CH2:31]2)=[O:3])=[CH:5][CH:6]=1)=[O:9]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To a three-necked 1-L flask was added 4-carboxybenzaldehyde (4.77 g, 31.8 mmol), EDC (6.64 g, 34.7 mmol), HOBT (1.91 g, 31.8 mmol), and DCM (200 mL). When the mixture was homogenous, a solution of biphenyl-2-ylcarbamic acid 1-(2-methylaminoethyl)piperidin-4-yl ester (10 g, 31.8 mmol; prepared as in Preparation 4) in DCM (100 mL) was added slowly. The reaction mixture was stirred at room temperature for 16 hours and then washed with water (1×100 mL), 1N HCl (5×60 mL), 1N NaOH (1×100 mL) brine (1×50 mL), dried over sodium sulfate, filtered and concentrated to afford 12.6 g of the title compound (92% yield; 85% purity based on HPLC). MS m/z: [M+H+] calcd for C29H31N3O4, 486.2; found, 486.4. Rf=3.12 min (10-70 ACN:H2O, reverse phase HPLC).
Workup
- washwashed with water (1×100 mL), 1N HCl (5×60 mL), 1N NaOH (1×100 mL) brine (1×50 mL)
- dry with materialdried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-df980df3e55a43f887950081b3db0cd6
- Source dataset
- uspto-grants-2011_01
- Patent number
- US07868175B2
Linked notes
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