Dimethylformamide → tert-butyl 4-(7-chloro-2-oxo-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-1-yl)piperidine-1-carboxylate

HRID 1026549Notes

Reaction equation

HRID 1026549 reaction equation
CN(C)C=O.[Cl:6][CH:7]1[CH2:12][NH:11][CH:10]([OH:13])[CH:9]([NH:14][CH:15]2[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][CH2:16]2)[CH2:8]1.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:35][C:36](Cl)=[O:37]>C(OCC)(=O)C.O>[Cl:6][C:7]1[CH:12]=[N:11][C:10]2[O:13][CH2:35][C:36](=[O:37])[N:14]([CH:15]3[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][CH2:16]3)[C:9]=2[CH:8]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 6577Chloroacetyl chlorideHCID 11430Potassium CarbonateHCID 68006279Tert-butyl 4-[(5-chloro-2-hydroxypiperidin-3-yl)amino]piperidine-1-carboxylate

Product 1

HCID 68006248tert-butyl 4-(7-chloro-2-oxo-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-1-yl)piperidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To an N,N-dimethylformamide suspension (60 ml) of tert-butyl 4-[(5-chloro-2-hydroxypiperidin-3-yl)amino]piperidine-1-carboxylate (3.00 g) and potassium carbonate (3.79 g) was added chloroacetyl chloride (1.09 ml), followed by stirring at room temperature for 30 minutes, and at 140° C. for 4 hours. After the reaction solution was brought back to room temperature, water and ethyl acetate were added, and the solution was separated. The organic layer was washed with water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to afford tert-butyl 4-(7-chloro-2-oxo-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-1-yl)piperidine-1-carboxylate (1.33 g).

Workup

  1. waitat 140° C. for 4 hours
  2. customwas brought back to room temperature
  3. customthe solution was separated
  4. washThe organic layer was washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-50aff7c2e3de463ca574ac97a84e953b
Source dataset
uspto-grants-2014_05
Patent number
US08729095B2

Reaction notes

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