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 1026549ノート

反応式

HRID 1026549 の反応式
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

参加物

7

反応物 4

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

生成物 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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-50aff7c2e3de463ca574ac97a84e953b
出典データセット
uspto-grants-2014_05
特許番号
US08729095B2

反応ノート

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