Triethylamine → Methyl 3-[2-({4-[(2-methoxypyridin-4-yl)oxy]-2-(methylamino)phenyl}amino)-2-oxoethoxy]benzoate
Reaction equation
C(Cl)(=O)C(C)(C)C.[CH3:8][O:9][C:10]([C:12]1[CH:13]=[C:14]([CH:20]=[CH:21][CH:22]=1)[O:15][CH2:16][C:17]([OH:19])=O)=[O:11].C(N(CC)CC)C.[CH3:30][O:31][C:32]1[CH:37]=[C:36]([O:38][C:39]2[CH:40]=[C:41]([NH:46][CH3:47])[C:42]([NH2:45])=[CH:43][CH:44]=2)[CH:35]=[CH:34][N:33]=1>ClCCl>[CH3:30][O:31][C:32]1[CH:37]=[C:36]([O:38][C:39]2[CH:44]=[CH:43][C:42]([NH:45][C:17](=[O:19])[CH2:16][O:15][C:14]3[CH:13]=[C:12]([CH:22]=[CH:21][CH:20]=3)[C:10]([O:9][CH3:8])=[O:11])=[C:41]([NH:46][CH3:47])[CH:40]=2)[CH:35]=[CH:34][N:33]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
Pivaloyl chloride (1.74 mL, 14.2 mmol) was added dropwise to a solution of [3-(methoxycarbonyl)phenoxy]acetic acid produced in Example (1c) (3.27 g, 15.6 mmol) and triethylamine (1.97 mL, 14.2 mmol) in dichloromethane (40 mL) in a nitrogen atmosphere at 0° C. After one hour, a solution of 4-[(2-methoxypyridin-4-yl)oxy]-N2-methylbenzene-1,2-diamine produced in Example (16d) (3.46 g, 14.2 mmol) and triethylamine (1.97 mL, 14.2 mmol) in dichloromethane (40 mL) was added dropwise at 0° C., and the mixture was stirred at room temperature for two hours. The reaction mixture was concentrated under reduced pressure. Then, the residue was purified by silica gel chromatography (ethyl acetate) to obtain the title compound (4.81 g, 78%) as a pale brown oil.
Workup
- concentrationThe reaction mixture was concentrated under reduced pressure
- customThen, the residue was purified by silica gel chromatography (ethyl acetate)
Sources & evidence
- ORD record
- ord-8c78410083224c04b8f3f00b1be56ed0
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08946264B2
Reaction notes
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