Pyridine → HCID 59253270, compound

HRID 386892Notes

Reaction equation

HRID 386892 reaction equation
N1C=CC=CC=1.[C:7]([O:11][C:12](=[O:25])[NH:13][C:14]1[O:18][N:17]=[C:16]([C:19]([CH3:24])([CH3:23])[CH2:20][NH:21][CH3:22])[CH:15]=1)([CH3:10])([CH3:9])[CH3:8].[C:26](Cl)(=[O:28])[CH3:27]>C1COCC1>[C:7]([O:11][C:12](=[O:25])[NH:13][C:14]1[O:18][N:17]=[C:16]([C:19]([CH3:24])([CH3:23])[CH2:20][N:21]([C:26](=[O:28])[CH3:27])[CH3:22])[CH:15]=1)([CH3:10])([CH3:9])[CH3:8]

Participants

5

Reactant 3

HCID 1049Pyridine2×HCID 6367Acetyl chloride2×HCID 59253237HCID 59253237, compound

Product 1

HCID 59253270HCID 59253270, compoundYield 47.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Pyridine (0.055 mL, 0.68 mmol) is added to a solution of [3-(1,1-dimethyl-2-methylamino-ethyl)-isoxazol-5-yl]-carbamic acid tert-butyl ester (150.0 mg, 0.59 mmol) in THF (2.0 mL) followed by the addition of acetyl chloride (0.048 mL, 0.68 mmol). The reaction mixture is stirred at room temperature for 3 h. After this time, more pyridine (0.028 mL, 0.34 mmol) and more acetyl chloride (0.024 mL, 0.34 mmol) are added to the reaction mixture and stirred for another 1 h. After this time, the reaction mixture is quenched with saturated aqueous NaHCO3 solution and extracted with ethyl acetate twice. The organic extracts are combined and washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure. Purification by flash chromatography on silica gel using methanol/DCM provides 87.0 mg of the title compound. Yield: 47%. m/z 312 [M+H].

Workup

  1. stirringstirred for another 1 h
  2. customAfter this time, the reaction mixture is quenched with saturated aqueous NaHCO3 solution
  3. extractionextracted with ethyl acetate twice
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customPurification by flash chromatography on silica gel

Sources & evidence

ORD record
ord-d5db3cfd0a974419aa0c520ec3e8f768
Source dataset
uspto-grants-2013_02
Patent number
US08372874B2

Reaction notes

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