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 1026549노트

반응식

HRID 1026549 반응식
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

참가 물질

7

반응물 4

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

생성물 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

시약·촉매·용매 2

HCID 962Water용매HCID 8857Ethyl Acetate용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-50aff7c2e3de463ca574ac97a84e953b
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08729095B2

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