Triethylamine → HCID 57527888, compound
Reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=1[CH2:5][NH2:6].C(N(CC)CC)C.[N:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[CH2:24][CH2:25][NH2:26].[O:27]1CC[O:30][CH2:29][CH2:28]1>>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=1[CH2:5][NH:6][C:29](=[O:30])[C:28]([NH:26][CH2:25][CH2:24][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][N:18]=1)=[O:27]Participants
Procedure
2-Methoxybenzyl amine (5 mmol) was mixed with triethylamine (2 equiv.) in anhydrous Dioxane. Ethyl oxalyl chloride (1 equiv.) was added and the mixture was shaken at room temperature for 0.5-2 hours. Then 2-(2-pyridinyl)ethyl amine (1 equiv.) was added and the suspension was heated at 80° C. overnight. The solution was concentrated and the residue was dissolved in ethyl acetate and washed with water. The organic layer was dried by sodium sulfate and solvent was evaporated to give the crude product, which was purified by flash column chromatography to afford the title compound: yield 70%, m.p. 118-119° C.; m/e=314 [M+1]; 1H NMR (CDCl3): 3.02 (t, 2H), 3.76 (dt, 2H), 3.86 (s, 3H), 4.47 (d, 2H), 6.80-6.90 (m, 2H), 7.14-7.18 (m, 2H), 7.20-7.30 (m, 2H), 7.55-7.62 (m, 1H), 7.75-7.83 (m, 1H), 8.05-8.12 (m, 1H), 8.55-8.63 (m, 1H).
Workup
- temperaturethe suspension was heated at 80° C. overnight
- concentrationThe solution was concentrated
- dissolutionthe residue was dissolved in ethyl acetate
- washwashed with water
- dry with materialThe organic layer was dried by sodium sulfate and solvent
- customwas evaporated
- customto give the crude product, which
- customwas purified by flash column chromatography
Sources & evidence
- ORD record
- ord-dafe20d8de944c33a1e8b67d6553fcb9
- Source dataset
- uspto-grants-2012_04
- Patent number
- US08148536B2
Reaction notes
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