Potassium Carbonate → HCID 67494869, compound

HRID 1504315Notes

Reaction equation

HRID 1504315 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

HCID 11430Potassium CarbonateHCID 783082-Chloro-5-nitropyridineHCID 2756811(R)-1-Boc-3-methylpiperazine

Product 1

HCID 67494869HCID 67494869, compoundYield 68.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
100 °C

Procedure

In each of two separate reactions, 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 (1.31 g, 9.46 mmol) in DMSO (20 mL) was heated at 100° C. overnight. The reaction mixtures were cooled to RT, filtered through silica gel, and 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 (40 g silica gel, 0-60% EtOAc/Hexanes). Desired fractions were combined and concentrated to provide the title intermediate (1.39 g each) as a yellowish solid. (m/z): [M+H]+ calcd for C15H22N4O4 323.16. found 323.3.

Workup

  1. customIn each of two separate reactions
  2. customThe reaction mixtures
  3. temperaturewere cooled to RT
  4. filtrationfiltered through silica gel
  5. washeluted with EtOAc (150 mL)
  6. washThe filtrate was washed with water (2×20 mL) and brine (20 mL)
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customto give a brownish oil, which
  11. customwas purified by silica gel chromatography (40 g silica gel, 0-60% EtOAc/Hexanes)
  12. concentrationconcentrated

Sources & evidence

ORD record
ord-a44c790c1c444f72a4c5a323592b7be7
Source dataset
uspto-grants-2015_12
Patent number
US09212168B2

Reaction notes

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