4-Formylbenzoic acid → HCID 59340335, compound
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.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH2:36][CH2:37][CH2:38][N:39]1[CH2:44][CH2:43][CH:42]([O:45][C:46](=[O:60])[NH:47][C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][C:49]=2[C:54]2[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=2)[CH2:41][CH2:40]1.CCN(C(C)C)C(C)C>C(Cl)Cl>[CH:8]([C:7]1[CH:10]=[CH:11][C:4]([C:1]([NH:36][CH2:37][CH2:38][N:39]2[CH2:44][CH2:43][CH:42]([O:45][C:46](=[O:60])[NH:47][C:48]3[CH:53]=[CH:52][CH:51]=[CH:50][C:49]=3[C:54]3[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=3)[CH2:41][CH2:40]2)=[O:3])=[CH:5][CH:6]=1)=[O:9]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of 4-carboxybenzaldehyde (0.95 g, 6.35 mmol) and HATU (3.02 g, 7.94 mmol) in 55 mL of DCM was stirred at room temperature for 1 hour and then biphenyl-2-ylcarbamic acid 1-(2-aminoethyl)piperidin-4-yl ester (3 g, 5.29 mmol; prepared as described in Preparation 7) and DIPEA (4.6 mL, 26.45 mmol) were added. The resulting mixture was stirred at room temperature for 2 hours and then diluted with 100 mL of DCM and washed with saturated sodium bicarbonate (150 mL) and brine (150 mL). The organic layer was dried over MgSO4, filtered and concentrated to provide 2.3 g of the title intermediate (92% yield), which was suitable for use without further purification.
Workup
- stirringThe resulting mixture was stirred at room temperature for 2 hours
- washwashed with saturated sodium bicarbonate (150 mL) and brine (150 mL)
- dry with materialThe organic layer was dried over MgSO4
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-7ebb92812fde48a19bd1b1ddbf7d6b82
- Source dataset
- uspto-grants-2013_03
- Patent number
- US08399488B2
Reaction notes
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