Potassium Carbonate → HCID 67494869, compound
Reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.[C:11]([O:15][C:16]([N:18]1[CH2:23][CH2:22][NH:21][C@H:20]([CH3:24])[CH2:19]1)=[O:17])([CH3:14])([CH3:13])[CH3:12].C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[C:11]([O:15][C:16]([N:18]1[CH2:23][CH2:22][N:21]([C:2]2[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=2)[C@H:20]([CH3:24])[CH2:19]1)=[O:17])([CH3:14])([CH3:12])[CH3:13]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
A mixture of 2-chloro-5-nitropyridine (1.0 g, 6.3 mmol), (R)-3-methyl-piperazine-1-carboxylic acid tert-butyl ester (1.4 g, 6.9 mmol) and potassium carbonate (1.308 g, 9.46 mmol) in DMSO (20 mL) was heated at 100° C. overnight. The reaction mixture was cooled to RT, and filtered through a pad of silica gel, eluted with EtOAc (150 mL). The filtrate was washed with water (2×20 mL) and brine (20 mL), dried over sodium sulfate, filtered and concentrated to give a brownish oil which was purified by silica gel chromatography (80 g silica gel, 0-60% EtOAc/hexanes). Desired fractions were combined and concentrated to give the title intermediate as a yellowish solid. (m/z): [M+H]+ calcd for C15H22N4O4 323.16 found 323.3.
Workup
- temperatureThe reaction mixture was cooled to RT
- filtrationfiltered through a pad of silica gel
- washeluted with EtOAc (150 mL)
- washThe filtrate was washed with water (2×20 mL) and brine (20 mL)
- dry with materialdried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated
- customto give a brownish oil which
- customwas purified by silica gel chromatography (80 g silica gel, 0-60% EtOAc/hexanes)
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-e0f5e4c9d7654a959a3540251919ad9a
- Source dataset
- uspto-grants-2016_02
- Patent number
- US09260414B2
Reaction notes
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