Pyridine → HCID 66874258, compound

HRID 249900Notes

Reaction equation

HRID 249900 reaction equation
[CH3:1][C@H:2]1[CH2:7][NH:6][CH2:5][C@H:4]([CH3:8])[N:3]1[C:9]1[O:10][C:11]2[C:12](=[C:14]([C:18]([O:20][CH3:21])=[O:19])[CH:15]=[CH:16][CH:17]=2)[N:13]=1.N1C=CC=CC=1.[C:28](Cl)(=[O:30])[CH3:29]>C(Cl)Cl>[C:28]([N:6]1[CH2:5][C@H:4]([CH3:8])[N:3]([C:9]2[O:10][C:11]3[C:12](=[C:14]([C:18]([O:20][CH3:21])=[O:19])[CH:15]=[CH:16][CH:17]=3)[N:13]=2)[C@@H:2]([CH3:1])[CH2:7]1)(=[O:30])[CH3:29]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 66873655HCID 66873655, compound

Product 1

HCID 66874258HCID 66874258, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To an ice-cold solution of methyl 2-((2S,6S)-2,6-dimethylpiperazin-1-yl)benzoxazole-4-carboxylate (273 mg, 0.943 mmol) in CH2Cl2 (5 mL) was added pyridine (0.114 mL, 1.41 mmol) followed by acetyl chloride (0.100 mL, 1.41 mmol) under an atmosphere of nitrogen. The mixture stirred for 18 h while gradually warming to room temperature. The reaction was diluted with CH2Cl2 (10 mL) and washed with saturated aqueous NaHCO3 solution (10 mL), 1 N HCl solution (10 mL), and brine (10 mL). The organic layer was dried (Na2SO4), filtered, and concentrated under reduced pressure. The resulting residue was purified by column chromatography over silica gel (0% to 50%, 95:15:1.5, CH2Cl2/CH3OH/concentrated NH4OH in CH2Cl2) to give methyl 2-((2S,6S)-4-acetyl-2,6-dimethylpiperazin-1-yl)benzoxazole-4-carboxylate as an oil (62.1 mg, 20%). 1H NMR and MS consistent.

Workup

  1. washwashed with saturated aqueous NaHCO3 solution (10 mL), 1 N HCl solution (10 mL), and brine (10 mL)
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by column chromatography over silica gel (0% to 50%, 95:15:1.5, CH2Cl2/CH3OH/concentrated NH4OH in CH2Cl2)

Sources & evidence

ORD record
ord-ef1ae94335564d208718eb7aba4b6416
Source dataset
uspto-grants-2011_01
Patent number
US07863271B2

Reaction notes

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