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Acetic Acid → tert-butyl 4-(3-acetyl-2-oxo-2H-pyrano[2,3-b]pyridin-7-yl)-1,4-diazepane-1-carboxylate

HRID 2206336
ノート
印刷プレビュー

反応式

HRID 2206336 の反応式
[CH:1]([C:3]1[CH:4]=[CH:5][C:6]([N:10]2[CH2:16][CH2:15][CH2:14][N:13]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:12][CH2:11]2)=[N:7][C:8]=1[OH:9])=O.N1CCCCC1.C(O)(=O)C.[C:34](OCC)(=[O:39])[CH2:35][C:36]([CH3:38])=[O:37]>CCO>[C:36]([C:35]1[C:34](=[O:39])[O:9][C:8]2=[N:7][C:6]([N:10]3[CH2:16][CH2:15][CH2:14][N:13]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:12][CH2:11]3)=[CH:5][CH:4]=[C:3]2[CH:1]=1)(=[O:37])[CH3:38]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 176Acetic AcidHCID 8082PiperidineHCID 8868Ethyl AcetoacetateHCID 178452079Tert-butyl 4-(5-formyl-6-hydroxypyridin-2-yl)-1,4-diazepane-1-carboxylate

生成物 1

HCID 89783253tert-butyl 4-(3-acetyl-2-oxo-2H-pyrano[2,3-b]pyridin-7-yl)-1,4-diazepane-1-carboxylate収率 62.1%

試薬・触媒・溶媒 1

HCID 702
Ethanol
溶媒

反応条件

温度
90 °C

実験手順

To a solution of tert-butyl 4-(5-formyl-6-hydroxypyridin-2-yl)-1,4-diazepane-1-carboxylate (600 mg, 1.87 mmol) in EtOH (4 mL) were treated with piperidine (239 mg, 2.8 mmol), acetic acid (511 mg, 9.35 mmol) and ethyl acetoacetate (487 mg, 3.74 mmol) at room temperature. The reaction mixture was stirred at 90° C. for 3 hours. The mixture was concentrated, quenched with a saturated NaHCO3 solution and extracted with dichloromethane three times. The combined organic layers were combined, dried over K2CO3, filtered and concentrated. The residue was purified on silica gel with methanol (0-10%) in dichloromethane to provide tert-butyl 4-(3-acetyl-2-oxo-2H-pyrano[2,3-b]pyridin-7-yl)-1,4-diazepane-1-carboxylate (450 mg, 62%). MS m/z 388 [M+H]+.

後処理

  1. concentrationThe mixture was concentrated
  2. customquenched with a saturated NaHCO3 solution
  3. extractionextracted with dichloromethane three times
  4. dry with materialdried over K2CO3
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified on silica gel with methanol (0-10%) in dichloromethane

出典と根拠

ORDレコード
ord-11585661b2e34f18b0a9e221dc02c5bd
出典データセット
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09371336B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート