1,2-Dichloroethane → Methyl 3-[(methylamino)carbonyl]-5-(5-methylpyridin-2-yl)benzoate
Reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([CH:11]=[C:12]([C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][N:15]=2)[CH:13]=1)[C:8](O)=[O:9])=[O:4].N.O1CCOCC1.C(Cl)CCl.C1C=CC2N(O)N=[N:38][C:36]=2C=1.C(N(CC)C(C)C)(C)C>CN(C)C=O>[CH3:36][NH:38][C:8]([C:7]1[CH:6]=[C:5]([CH:13]=[C:12]([C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][N:15]=2)[CH:11]=1)[C:3]([O:2][CH3:1])=[O:4])=[O:9]Participants
8
Reactant 6
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 3-(methoxycarbonyl)-5-(5-methylpyridin-2-yl)benzoic acid (1.85 g, 6.82 mmol) in N,N-dimethylformamide (20 mL) was added 2 M ammonia in dioxane (10.2 mL, 20.4 mmol), EDC (2.61 g, 13.6 mmol), HOBT (2.09 g, 13.6 mmol) and N,N-diisopropylethylamine (4.76 mL, 27.3 mmol). After 16 h, the reaction was concentrated and the residue was dissolved in 200 ml of dichloromethane. The mixture was washed with 100 mL of saturated aqueous sodium bicarbonate solution (2×) and brine (100 ml). The combined organic extracts were dried over sodium sulfate, filtered and concentrated. The residue was purified by silica gel chromatography (1% ethyl acetate/hexane→60% ethyl acetate/hexane) to give the title compound (1.82 g). MS 285.1 (M+1).
Workup
- concentrationthe reaction was concentrated
- dissolutionthe residue was dissolved in 200 ml of dichloromethane
- washThe mixture was washed with 100 mL of saturated aqueous sodium bicarbonate solution (2×) and brine (100 ml)
- dry with materialThe combined organic extracts were dried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated
- customThe residue was purified by silica gel chromatography (1% ethyl acetate/hexane→60% ethyl acetate/hexane)
Sources & evidence
- ORD record
- ord-56d7b4349c594464979d9dc1d0a41253
- Source dataset
- uspto-grants-2012_08
- Patent number
- US08247401B2
Reaction notes
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