N,N'-Dimethylethylenediamine → HCID 86724965, compound
Reaction equation
[CH3:1][O:2][CH2:3][O:4][CH2:5][C@@H:6]1[CH2:10][NH:9][C:8](=[O:11])[CH2:7]1.Br[C:13]1[CH:14]=[CH:15][C:16]2[O:21][CH2:20][C:19](=[O:22])[NH:18][C:17]=2[CH:23]=1.CNCCNC.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.[Cu](I)I.CO.ClCCl>[CH3:1][O:2][CH2:3][O:4][CH2:5][C@@H:6]1[CH2:10][N:9]([C:13]2[CH:14]=[CH:15][C:16]3[O:21][CH2:20][C:19](=[O:22])[NH:18][C:17]=3[CH:23]=2)[C:8](=[O:11])[CH2:7]1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 4
Conditions
- Temperature
- 100 °C
Procedure
Copper iodide (1.50 g, 7.85 mmol) was added at room temperature to a suspension of (4S)-4-[(methoxymethoxy)methyl]pyrrolidin-2-one (3.00 g, 18.8 mmol), 6-bromo-2H-1,4-benzoxazin-3(4H)-one (3.58 g, 15.7 mmol) and N,N′-dimethylethylenediamine (0.84 ml, 7.85 mmol) and potassium carbonate (6.51 g, 47.1 mmol) in toluene (60 ml) and the mixture was heated to 100° C. The mixture was stirred at the same temperature for 42 hours and dichloromethane (100 ml) and methanol (10 ml) were then added thereto to dilute the reaction solution, and the insoluble material was removed by filtration. The filtrate was concentrated and the obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate) to yield 1.92 g (40%) of the title compound in the form of a light yellow solid.
Workup
- additionto dilute the reaction solution
- customthe insoluble material was removed by filtration
- concentrationThe filtrate was concentrated
- customthe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate)
Sources & evidence
- ORD record
- ord-9123647d2d5a4cc994243a54d739d4db
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08952010B2
Reaction notes
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