Pyridine → (S)-1-(4-Chloro-phenyl)-6-oxo-piperidine-2-carboxylic acid (3-tert-butyl-isoxazol-5-yl)-amide

HRID 336200Notes

Reaction equation

HRID 336200 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:13](=[O:14])[CH2:12][CH2:11][CH2:10][C@H:9]2[C:15]([OH:17])=O)=[CH:4][CH:3]=1.[NH2:18][C:19]1[O:23][N:22]=[C:21]([C:24]([CH3:27])([CH3:26])[CH3:25])[CH:20]=1.N1C=CC=CC=1.P(Cl)(Cl)(Cl)=O>O>[C:24]([C:21]1[CH:20]=[C:19]([NH:18][C:15]([C@@H:9]2[CH2:10][CH2:11][CH2:12][C:13](=[O:14])[N:8]2[C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)=[O:17])[O:23][N:22]=1)([CH3:27])([CH3:26])[CH3:25]

Participants

6

Reactant 4

HCID 1049PyridineHCID 24813Phosphorus oxychlorideHCID 20956943-Tert-butyl-1,2-oxazol-5-amineHCID 42127104(S)-1-(4-Chloro-phenyl)-6-oxo-piperidine-2-carboxylic acid

Product 1

HCID 58563752(S)-1-(4-Chloro-phenyl)-6-oxo-piperidine-2-carboxylic acid (3-tert-butyl-isoxazol-5-yl)-amide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To a cold slurry of (S)-1-(4-Chloro-phenyl)-6-oxo-piperidine-2-carboxylic acid (0.2 g; 0.788 mmol) and 5-amino-3-tert-butylisoxazole (0.110 g; 0.788 mmol) in pyridine (0.956 mL; 11.820 mmol) is added phosphorous oxychloride (0.088 mL; 0.946 mmol). The mixture is stirred at 0° C. for 30 minutes and then diluted with water and extracted with ethyl acetate several times. The organics are combined and washed with water and brine, dried (Na2SO4), filtered and concentrated in vacuo. Purification by preparative HPLC affords title compound, m/z 376 [M+H+].

Workup

  1. extractionextracted with ethyl acetate several times
  2. washwashed with water and brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification by preparative HPLC

Sources & evidence

ORD record
ord-cc60fa4f3eba4880b745e202d0cd6112
Source dataset
uspto-grants-2014_11
Patent number
US08889670B2

Reaction notes

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