Triethylamine → HCID 19029324, compound
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]2[CH2:15][C:14](=[O:16])[O:13][C:11](=[O:12])[CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].[F:17][C:18]([F:32])([F:31])[C:19]1[CH:20]=[C:21]([CH:24]=[C:25]([C:27]([F:30])([F:29])[F:28])[CH:26]=1)[CH2:22][NH2:23].[CH2:33](N(CC)CC)C>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([CH2:10][C:11]([N:23]([CH2:22][C:21]2[CH:20]=[C:19]([C:18]([F:31])([F:32])[F:17])[CH:26]=[C:25]([C:27]([F:30])([F:28])[F:29])[CH:24]=2)[CH3:33])=[O:12])[CH2:15][C:14]([OH:13])=[O:16])[CH:5]=[CH:6][C:7]=1[Cl:8]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
3-(3,4-Dichlorophenyl)glutaric anhydride (3.1 g, Example 1, Step C) in CH2Cl2 (50 mL) at 0° C. was treated sequentially with 3,5-bis-(trifluoromethyl)benzylamine (3.4 g), triethylamine (1.83 mL) and N,N-dimethylaminopyridine (150 mg). The mixture was stirred at 0° C. for two hours then allowed to warm to room temperature and stirred for 12 hours. The reaction mixture was diluted with CH2Cl2 (200 mL) and washed with 1N HCl (1×100 mL) and water (1×100 mL). The organic layers were dried over MgSO4, filtered and concentrated to afford the title compound (6.1 g).
Workup
- temperatureto warm to room temperature
- stirringstirred for 12 hours
- washwashed with 1N HCl (1×100 mL) and water (1×100 mL)
- dry with materialThe organic layers were dried over MgSO4
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-8cda20053ef342ac8ecff8ba13052a99
- Source dataset
- uspto-grants-1997_08
- Patent number
- US05654316
Reaction notes
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